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Environmentally-friendly synthetic method of pyrimidine compound

A synthesis method and compound technology, which is applied in the synthesis field of pyrimidine compounds, can solve problems such as difficult recovery of catalysts, unfriendly solvent environment, and strong corrosion of equipment, so as to reduce pollution and corrosion of equipment, and the product yield is not affected. Effect, yield and effect of high product purity

Inactive Publication Date: 2011-11-16
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In order to solve a series of problems in the existing technology for preparing pyrimidine compounds, such as large amount of catalyst used, strong corrosion of equipment, difficult recovery of catalyst, and unfriendly solvents used, and to advocate a greener and more efficient synthesis concept, the present invention The purpose is to disclose a kind of sulfonic acid type acidic ionic liquid as a catalyst, under solvent-free conditions, the synthesis method of pyrimidine compound promoted by microwave

Method used

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  • Environmentally-friendly synthetic method of pyrimidine compound
  • Environmentally-friendly synthetic method of pyrimidine compound
  • Environmentally-friendly synthetic method of pyrimidine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Sulfonic acid type ionic liquid [(HSO 3 -p) 2 im][CF 3 SO 3 ] (0.02mmol) was added into a three-necked round-bottomed flask, benzaldehyde (25mmol), methyl acetoacetate (27.5mmol) and urea (37.5mmol) were added to the reaction vessel successively, and under mechanical stirring, placed in microwave reaction In the container, react with microwave at 100°C for 10 minutes, cool to room temperature, pour the reaction solution into 30 mL of ice water and stir for 20 minutes, filter the mixed solution directly, and dry it. The yield is 97%. The structural formula is as follows:

[0028]

Embodiment 2

[0030] Sulfonic acid type ionic liquid [(HSO 3 -p) 2 im][CF 3 SO 3 ] (0.02mmol) joins in the three-necked round bottom flask, benzaldehyde (25mmol),

[0031] Ethyl acetoacetate (27.5mmol) and urea (37.5mmol) were successively added to the reaction vessel, placed in a microwave reactor under mechanical stirring, and microwaved at 100°C for 10 minutes, cooled to room temperature, and the reaction solution was poured into Stir in 30mL of ice water for 20 minutes, filter the mixture directly, and dry it with a yield of 98%. The structural formula is as follows:

[0032]

Embodiment 3

[0034] Sulfonic acid type ionic liquid [(HSO 3 -p) 2 im][CF 3 SO 3 ] (0.02mmol) joins in the three-necked round bottom flask, benzaldehyde (25mmol),

[0035] Methyl acetoacetate (27.5mmol) and thiourea (37.5mmol) were successively added to the reaction vessel, placed in a microwave reactor under mechanical stirring, and microwaved at 100°C for 15 minutes, cooled to room temperature, and the reaction solution poured Pour into 30mL of ice water and stir for 20 minutes, the mixture is directly filtered and dried with a yield of 90%. The structural formula is as follows:

[0036]

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Abstract

The invention relates to a synthetic method of a pyrimidine derivative. In the method, a sulphonic acid ion liquid is taken as a catalyst, aromatic aldehyde, methyl acetoacetate (ethyl ester) and urea (or thiourea) are taken as raw materials, and a reaction is undergone under the action of microwave irradiation under a solvent-free condition. The molar ratio of aldehyde serving as a reactant to ester serving as a reactant to urea serving as a reactant (or thiourea) is 1:(0.5-2):(0.5-2); the ratio of the sulphonic acid ion liquid to the aldehyde is 1:(10-50); the reaction time is 10-50 minutes; the reaction temperature is 50-120 DEG C; and the pressure is 1-1.3 MPa. The synthetic method has the characteristics of easiness in operation, readily-available raw materials, small number of reaction steps, high yield, reusable catalyst, environmental friendliness, and the like.

Description

technical field [0001] The present invention relates to a kind of synthetic method of pyrimidine compound Background technique [0002] Pyrimidine compounds have important uses in the fields of medicine and pesticides. Especially in recent years, pyrimidine compounds have calcium antagonistic activity, blood pressure reduction, α 1a - Antagonism and anti-cancer activities, in addition, it can also be used as a lead in the development of anti-cancer drugs and an intermediate of marine alkaloids. Therefore, the research on the synthesis of pyrimidine compounds has attracted great attention, and the Biginelli one-step condensation reaction to prepare pyrimidine compounds is considered to be the most economical and practical method. In the traditional Biginelli reaction method for synthesizing pyrimidines, commonly used catalysts include hydrochloric acid, trifluoroacetic acid, etc. Acid, FeCl 3 , InCl 3 Representative Lewis acids and solid acids are used as catalysts. In p...

Claims

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Application Information

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IPC IPC(8): C07D309/22C07D407/04C07D409/04
Inventor 李佰林
Owner TAIZHOU UNIV
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