JPH03127780A - Anilinopyrimidine derivative - Google Patents
Anilinopyrimidine derivativeInfo
- Publication number
- JPH03127780A JPH03127780A JP26710089A JP26710089A JPH03127780A JP H03127780 A JPH03127780 A JP H03127780A JP 26710089 A JP26710089 A JP 26710089A JP 26710089 A JP26710089 A JP 26710089A JP H03127780 A JPH03127780 A JP H03127780A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- general formula
- propynyl
- anilinopyrimidine derivative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000008059 anilinopyrimidines Chemical class 0.000 title claims description 12
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 17
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000012345 acetylating agent Substances 0.000 abstract description 3
- MPHBIDCNHVMYDD-UHFFFAOYSA-N 4-chloro-6-methyl-n-phenylpyrimidin-2-amine Chemical compound CC1=CC(Cl)=NC(NC=2C=CC=CC=2)=N1 MPHBIDCNHVMYDD-UHFFFAOYSA-N 0.000 abstract 1
- 230000002070 germicidal effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 2
- -1 pyrimidine compound Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- BHAKRVSCGILCEW-UHFFFAOYSA-N 2-chloro-4-methylpyrimidine Chemical compound CC1=CC=NC(Cl)=N1 BHAKRVSCGILCEW-UHFFFAOYSA-N 0.000 description 1
- KQRBOLDPRPDVIM-UHFFFAOYSA-N 2-prop-1-ynylpyrimidine Chemical compound CC#CC1=NC=CC=N1 KQRBOLDPRPDVIM-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 240000005109 Cryptomeria japonica Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、殺菌剤として有用なピリミジン誘導体の製造
中間体に関する。さらに詳細には、ヨーロッパ特許公開
２２４３３９号公報記載の殺菌剤＝１−
として公知の一般式
で示されるアニリノピリミジン誘導体の製造中間体とし
て有用なアニリノピリミジン誘導体に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to intermediates for producing pyrimidine derivatives useful as fungicides. More specifically, the present invention relates to an anilinopyrimidine derivative useful as an intermediate in the production of an anilinopyrimidine derivative represented by the general formula known as the fungicide =1- described in European Patent Publication No. 224339.
（従来の技術）
従来、前記−形式（ｎ）で示されるアニリノピリミジン
誘導体の製造方法としてはヨーロッパ特許公開２２４３
３９号公報に以下の方法が提案されている。(Prior Art) Conventionally, a method for producing an anilinopyrimidine derivative represented by the above-mentioned format (n) is disclosed in European Patent Publication No. 2243.
The following method is proposed in Publication No. 39.
−
［１）
（Ｍ）
（式中、Ｚはアルキル基を示す。）
（発明が解決しようとする課題）
しかし、この製造方法においては一般式（ｎｌ）で示さ
れるピリミジン化合物の入手が困難であり、他の方法で
一般式（ＩＩ）で示されるアニリノピリミジン類を製造
する方法が望まれていた。- [1) (M) (In the formula, Z represents an alkyl group.) (Problem to be solved by the invention) However, in this production method, it is difficult to obtain the pyrimidine compound represented by the general formula (nl). However, there has been a desire for a method for producing anilinopyrimidines represented by general formula (II) using other methods.
（課題を解決するための手段）
このような現状に鑑み本発明者らは工業的に収率よく一
般式（ＩＩ）で示されるアニリノピリミジ３
ン類を製造する方法を提供すべく鋭意研究を重ねた結果
、次に示される工程により製造することができることを
見出した。(Means for Solving the Problems) In view of the current situation, the present inventors have conducted extensive research in order to provide a method for industrially producing the anilinopyrimidines represented by the general formula (II) with a high yield. As a result, it was found that it can be manufactured by the following steps.
（Ｖり
〔■〕
〔■〕 〔■〕さらに上記反
応式中、一般式〔■〕および〔■〕で示されるアニリノ
ピリミジン誘導体が文献未記載の新規化合物であること
を見出し本発明を完成するに至った。なお、上記製造法
においてアセチル基のかわりに、スルホニル基、アルコ
キシカルボニル基等の電子吸引基を使用しても同様の結
果を得ることが出来る。(Vri [■] [■] [■] Furthermore, in the above reaction formula, it was discovered that the anilinopyrimidine derivatives represented by the general formulas [■] and [■] are new compounds that have not been described in literature, and the present invention was completed. Note that similar results can be obtained by using an electron-withdrawing group such as a sulfonyl group or an alkoxycarbonyl group in place of the acetyl group in the above production method.
すなわち本発明は、 一般式 （式中、Ｘは塩素原子または１−プロピニル基を示す。That is, the present invention general formula (In the formula, X represents a chlorine atom or a 1-propynyl group.
）で表されるアニリノピリミジン誘導体であ る。) is an anilinopyrimidine derivative represented by
本発明の化合物は前記一般式ＣＩ）で示されるアニリノ
ピリミジン誘導体であるが、式中Ｘは塩素原子または１
−プロピニル基を示す。The compound of the present invention is an anilinopyrimidine derivative represented by the general formula CI), where X is a chlorine atom or 1
- indicates a propynyl group.
本発明の化合物中、Ｘが塩素原子である化合物（前記反
応式中、一般式〔■〕で示される化合物）は、前記反応
式中、一般式（ＶＩ）で示される２−アニリノ−４−ク
ロロ−６−メチルピリミジンとアセチル化剤とを反応さ
せることにより製造することが出来る。この除用いるア
セチル化剤としては、塩化アセチルまたは無水酢酸であ
る。反応は、−
塩基（例えば、 トリエチルアミン、ピリジン、ジメチ
ルアニリン等の有機塩基、水素化ナトリウム。Among the compounds of the present invention, the compound in which X is a chlorine atom (the compound represented by the general formula [■] in the above reaction formula) is the 2-anilino-4- represented by the general formula (VI) in the above reaction formula. It can be produced by reacting chloro-6-methylpyrimidine and an acetylating agent. The acetylating agent used for this removal is acetyl chloride or acetic anhydride. The reaction can be carried out using - bases (e.g. organic bases such as triethylamine, pyridine, dimethylaniline, sodium hydride).
ナトリウムアミド等の無機塩基）の存在下、またルウジ
オキサン、テトラヒドロフラン等のエーテル類、アセト
ン、メチルエチルケトン、シクロヘキサノン等のケトン
類およびアセトニトリル、プロピオニル等のニトリル類
）中、または溶媒無しに行うことが出来る。反応温度は
、−２０’Ｃ〜溶媒の沸点の範囲、好ましくは室温から
１２０°Ｃの範囲で反応させることにより製造すること
が出来る。The reaction can be carried out in the presence of an inorganic base such as sodium amide, ethers such as roudioxane and tetrahydrofuran, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, and nitrites such as acetonitrile and propionyl), or without a solvent. The reaction temperature ranges from -20'C to the boiling point of the solvent, preferably from room temperature to 120C.
このようにして得られた２−（Ｎ−アセチルアニリノ）
−４−クロロ−６−メチルピリミジン〔■〕と１−プロ
ピンとを、触媒量の塩化ビス（トリフェニルホスフィン
）パラジウム（ｎ）およびヨウ化鋼（Ｉ）の存在下、
トリエチルアミン６
またはトリエチルアミン−溶媒（例えば、上述の化合物
〔■〕の製造の除用いた溶媒）中で反応させ、化合物〔
■〕を製造することが出来る。反応次に化合物〔■〕を
塩酸、臭化水素酸、硫酸等−＼
・９酸、または水酸化ナトリウム、水酸化カリウム、・
′
等のアルカリ金属水酸化物等の存在下、水とアルコール
、テトラヒドロフラン等の有機溶媒との混合溶媒中、０
℃から溶媒の沸点の温度範囲で加水分解することにより
、目的とする一般式（ＩＩ）で示される２−アニリノ−
４−メチル−６−（１−プロピニル）ピリミジンを得る
ことが出来る。2-(N-acetylanilino) thus obtained
-4-chloro-6-methylpyrimidine [■] and 1-propyne in the presence of catalytic amounts of bis(triphenylphosphine)palladium chloride (n) and steel iodide (I),
Triethylamine 6 or triethylamine is reacted in a solvent (e.g., the solvent used in the production of the above compound [■]) to form the compound [
■] can be manufactured. After the reaction, the compound [■] is mixed with hydrochloric acid, hydrobromic acid, sulfuric acid, etc. ＼ 9 acids, or sodium hydroxide, potassium hydroxide, ・
0 in a mixed solvent of water and an organic solvent such as alcohol or tetrahydrofuran in the presence of an alkali metal hydroxide such as
By hydrolyzing in the temperature range from °C to the boiling point of the solvent, the desired 2-anilino-
4-Methyl-6-(1-propynyl)pyrimidine can be obtained.
（発明の効果）
本発明の一般式（Ｉ）で示される化合物は、殺菌剤とし
て公知のアニリノピリミジン類の製造中間体として有用
な化合物であり、本発明化合物を原料として用いること
により、従来の製造方法に比ベニ業的に収率よく目的と
するアニリノピリミジン類を製造することが可能となっ
た。(Effects of the Invention) The compound represented by the general formula (I) of the present invention is a compound useful as an intermediate for producing anilinopyrimidines known as fungicides, and by using the compound of the present invention as a raw material, It has now become possible to produce the desired anilinopyrimidines in a commercially high yield compared to the production method described above.
７ （実施例） 次に実施例により、本発明を更に詳細に説明する。7 (Example) Next, the present invention will be explained in more detail with reference to Examples.
２−アニリノ−４−クロロ−６−メチルピリミジン２．
２ｇと、無水酢酸１０ｍ１をトルエン１０１１に溶解し
、還流下３時間撹拌した。次に反応液に水を加え、 ト
ルエン１００ｍ１で抽出した。 トルエン層を硫酸マグ
ネシウムで乾燥した後、トルエンを濃縮留去した。残渣
をシリカゲルカラムクロマトグラフィーにより精製し、
融点５５〜５７℃の目的化合物２．０ｇ（収率７７％）
を得た。2-anilino-4-chloro-6-methylpyrimidine2.
2 g and 10 ml of acetic anhydride were dissolved in 1,011 l of toluene and stirred under reflux for 3 hours. Next, water was added to the reaction solution, and the mixture was extracted with 100 ml of toluene. After drying the toluene layer with magnesium sulfate, toluene was concentrated and distilled off. The residue was purified by silica gel column chromatography,
2.0 g of the target compound with a melting point of 55-57°C (yield 77%)
I got it.
−
実施例２ ２−（Ｎ−アセプルアニリノ）−４明メチ
ル−６−（１−プロピニル）ピリミジンの製造
ドライアイス−アセトントラップ、潟度肝を付ルアく７
２０ｍ１．アセトニトリル２０ｍ１を加え、５０℃にて
撹拌しながらプロピン０．４ｇを１０分かけて吹き込ん
だ。吹き込み後さらに１．５時間撹拌し、反応液に水を
加え、 トルエンで抽出した。 トルエン層を硫酸マグ
ネシウムで乾燥した後、 トルエンを濃縮留去した。残
渣をシリカゲルカラムクロマトグラフィーにより精製し
、目的化合物１．７ｇ（収率９０％）を得た。椙：
１．５８５８９一
実施例３２−アニリノ−４−メチル−６−（１−プロピ
ニル）ピリミジンの製造
２−（Ｎ−アセチルアニリノ）−４−メチル−６−（１
−プロピニル）ピリミジン０．８ｇをエタ、炭酸ナトリ
ウムでｐＨ９とした後、酢酸エチルで＼１１＼
有機層を抽出し、硫酸マグネシウムで乾燥した。- Example 2 Preparation of 2-(N-acepluanilino)-4-methyl-6-(1-propynyl)pyrimidine Dry ice-acetone trap, lagoon chloride 7
20m1. 20 ml of acetonitrile was added, and 0.4 g of propyne was blown in over 10 minutes while stirring at 50°C. After bubbling, the mixture was further stirred for 1.5 hours, water was added to the reaction mixture, and the mixture was extracted with toluene. After drying the toluene layer with magnesium sulfate, toluene was concentrated and distilled off. The residue was purified by silica gel column chromatography to obtain 1.7 g (yield 90%) of the target compound. Sugi:
1.58589 Example 3 Preparation of 2-anilino-4-methyl-6-(1-propynyl)pyrimidine 2-(N-acetylanilino)-4-methyl-6-(1
-Propynyl)pyrimidine was adjusted to pH 9 with ethyl acetate and sodium carbonate, and the organic layer was extracted with ethyl acetate and dried over magnesium sulfate.
酢酸エチルを濃縮留去し、残渣をヘキサンで洗浄して融
点１２５〜１２７℃の目的化合物０．６ｇ（収率８６％
）を得た。Ethyl acetate was concentrated and distilled off, and the residue was washed with hexane to obtain 0.6 g of the target compound with a melting point of 125-127°C (yield 86%).
) was obtained.
実施例４２−アニリノ−４−メチル−６−（１−プロビ
ニル）ピリミジンの製造
２−（Ｎ−アセチルアニリノ）−４−メチル６−（１−
プロピニル）ピリミジン０．８ｇをテトラヒドロフラン
２０ｍ１に溶解し、これに１０％苛性ソーダ水溶液７ｍ
ｌを加え、還流下４時間撹拌した。反応液に水を加え、
酢酸エチルで抽出し、硫酸マグネシウムで乾燥した後、
酢酸エチルを濃縮０
留去した。Example 4 Preparation of 2-anilino-4-methyl-6-(1-provinyl)pyrimidine 2-(N-acetylanilino)-4-methyl 6-(1-
Dissolve 0.8 g of propynyl pyrimidine in 20 ml of tetrahydrofuran, and add 7 ml of 10% caustic soda aqueous solution to this.
1 was added thereto, and the mixture was stirred under reflux for 4 hours. Add water to the reaction solution,
After extraction with ethyl acetate and drying with magnesium sulfate,
Ethyl acetate was distilled off to zero concentration.
残渣をシリカゲルカラムク トゲラ フィーにより精製し、 融点１ ２５〜 ２７℃目的 化合物０．５ｇ（収率７１％） を得た。Column the residue with silica gel Togera Refined by fee, Melting point 1 25～ 27℃ purpose Compound 0.5g (yield 71%) I got it.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26710089A JPH03127780A (en) | 1989-10-13 | 1989-10-13 | Anilinopyrimidine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26710089A JPH03127780A (en) | 1989-10-13 | 1989-10-13 | Anilinopyrimidine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03127780A true JPH03127780A (en) | 1991-05-30 |
Family
ID=17440057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26710089A Pending JPH03127780A (en) | 1989-10-13 | 1989-10-13 | Anilinopyrimidine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03127780A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993021162A1 (en) * | 1992-04-15 | 1993-10-28 | Nissan Chemical Industries, Ltd. | 2-arylaminopyrimidinone derivative, and herbicide and plant growth regulator |
| US8944836B2 (en) | 2012-01-10 | 2015-02-03 | Nichifu Terminal Industries Co., Ltd. | Wire line connector |
-
1989
- 1989-10-13 JP JP26710089A patent/JPH03127780A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993021162A1 (en) * | 1992-04-15 | 1993-10-28 | Nissan Chemical Industries, Ltd. | 2-arylaminopyrimidinone derivative, and herbicide and plant growth regulator |
| US5518994A (en) * | 1992-04-15 | 1996-05-21 | Nissan Chemical Industries, Ltd. | 2-arylaminopyrimidinone derivative, and herbicide and plant growth regulator |
| CN1041724C (en) * | 1992-04-15 | 1999-01-20 | 日产化学工业株式会社 | 2-arylaminopyrimidinone derivative, and herbicide and plant growth regulator using the same |
| US8944836B2 (en) | 2012-01-10 | 2015-02-03 | Nichifu Terminal Industries Co., Ltd. | Wire line connector |
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