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Aryl pyrimidine ortho-position monocyano compounds and synthesis method thereof

A technology of arylpyrimidine and compound, applied in the field of arylpyrimidine ortho-monocyano compound and its synthesis, can solve the problem that yield and conversion rate are not very high, arylpyrimidine ortho-monocyanation reaction has not been reported, etc. problems, to achieve the effect of moderate conditions, simple operation and good development prospects

Inactive Publication Date: 2013-12-25
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] In summary, there are several methods for preparing aryl pyrimidine ortho monocyano compounds, but the yield and conversion rate are not very high, and the above-mentioned Several methods have not been reported for the ortho monocyanylation of arylpyrimidines with substituents

Method used

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  • Aryl pyrimidine ortho-position monocyano compounds and synthesis method thereof
  • Aryl pyrimidine ortho-position monocyano compounds and synthesis method thereof
  • Aryl pyrimidine ortho-position monocyano compounds and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Preparation of 2-(2-cyano-4-methoxyphenyl)pyrimidine

[0035] 2-(2-cyano-4-methoxyphenyl)pyrimidine adopts the following steps: 1. add 18.60 grams of 2-(4-methoxyphenyl)pyrimidine in 1000 milliliters of reactor, 1.23 grams of [RhCp * Cl 2 ] 2 , 2.75 grams of silver hexafluoroantimonate, 58.00 grams of copper trifluoroacetate, 16.60 grams of tert-butylisonitrile, 500 milliliters of 1,2-dichloroethane, heated to 130 ° C. Use thin layer chromatography to track the reaction until the raw materials disappear; ② After the reaction, add 3 M ammonia solution to the system, extract the product with ethyl acetate, and remove the solvent with a rotary evaporator after drying to obtain a crude product; ③ The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 5: 1) to obtain 15.82 g of 2-(2-cyano-4-methoxyphenyl) with a yield of 75%. Melting point: 128-129°C.

[0036] –1 ): 3079, 2979, 2222, 1606, 1552, 1416, 1289, 1054, 889, 80...

Embodiment 2

[0041] Example 2: Preparation of 2-(2-cyano-4-chlorophenyl)pyrimidine

[0042] 2-(2-cyano-4-chlorophenyl)pyrimidine adopts the following steps: 1. add 15.24 grams of 2-(4-chlorophenyl)pyrimidine in 1000 milliliters of reactor, 0.49 grams of [RhCp * Cl 2 ] 2 , 1.10 g of silver hexafluoroantimonate, 46.40 g of copper trifluoroacetate, 13.28 g of tert-butylisonitrile, 400 ml of 1,2-dichloroethane, heated to 130°C. Use thin layer chromatography to track the reaction until the reaction raw materials disappear; ② After the reaction, add 3 M ammonia solution to the system, extract the product with ethyl acetate, and remove the solvent with a rotary evaporator after drying to obtain a crude product; ③ The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 5: 1) to obtain 12.76 g of 2-(2-cyano-4-chlorophenyl) with a yield of 74%. Melting point: 212-214°C.

[0043] –1 ): 3083, 3032, 2231, 1573, 1415, 1383, 807, 634.

[0044] 1 H NMR (CDC...

Embodiment 3

[0048] Example 3: Preparation of 2-(2-cyano-4-p-toluenesulfonate phenyl)pyrimidine

[0049] 2-(2-cyano-4-p-toluenesulfonate phenyl) pyrimidine adopts the following steps: 1. add 22.82 grams of 2-(4-p-toluenesulfonate phenyl) pyrimidine in 1000 ml reactor, 0.861 g [RhCp * Cl 2 ] 2 , 1.93 g of silver hexafluoroantimonate, 60.90 g of copper trifluoroacetate, 17.43 g of tert-butylisonitrile, 350 ml of 1,2-dichloroethane, heated to 130°C. Use thin layer chromatography to track the reaction until the reaction raw materials disappear; ② After the reaction, add 3 M ammonia solution to the system, extract the product with ethyl acetate, and remove the solvent with a rotary evaporator after drying to obtain a crude product; ③ The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 5: 1) to obtain 20.64 g of 2-(2-cyano-4-p-toluenesulfonylphenyl) with a yield of 84%. Melting point: 135-137°C.

[0050] -1 3073, 3035, 2222, 1576, 1553, 1418, 1376, 1...

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PUM

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Abstract

The invention relates to aryl pyrimidine ortho-position monocyano compounds and a synthesis method thereof. The structural formula of the compounds is shown in the specification, wherein R1=CH3, OCH3, Cl or OTs, and R2=H, C2H5 or Ph. The aryl pyrimidine ortho-position monocyano compounds provided by the invention are important intermediates for organic synthesis, and have potential pharmaceutical activity and material characteristics. The method has the advantages of accessible raw materials, conventional reaction solvent, moderate conditions and environment-friendly reaction, and is very simple to operate; the tert-butyl isonitrile used as the cyano source has the best reaction activity under catalytic action of rhodium; the maximum yield is up to 90%; and thus, the method has favorable development prospects in industrial production.

Description

Technical field [0001] The present invention involves a ticorine derivative and its synthesis method, especially a monocyline cyanocytic compound and its synthetic method. Background technique [0002] Cyanomyal compounds exist in nature and are very important compounds in organic synthesis.Organic cyanide is not only an important drug intermediate, but also an important structure of pigment dye, but they are easily converted into other useful functional groups such as aldehyde, ketone, carboxylic acid, amine, and amide.The formation of cyanion in the formation of carbon -carbon bonds to organic compounds is one of the most basic methods in organic synthesis.Since the gardenic skeleton exists in many commercially available drugs, this type of compound also has potential drug activity.For example, CITALOPRAM (CITALOPRAM), mental inhibitory cyamemazine, and the treatment of breast cancer, Fadrozole, and Letrozole, all contain the diarrhea skeleton.In addition, cyanocytic compounds ...

Claims

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Application Information

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IPC IPC(8): C07D239/26
Inventor 许斌洪小虎王浩钱光印刘秉新
Owner SHANGHAI UNIV
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