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Room temperature solvent-free synthesis of 3,4-dihydropyrimidine-2-ketone

A synthesis method, dihydropyrimidine technology, applied in 3 fields, can solve the problems of not meeting the requirements of green chemistry, long reaction time, low yield, etc., and achieve the effect of low production cost, simple operation and good product purity

Inactive Publication Date: 2012-09-26
山东兴安智慧科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many reported methods have drawbacks, such as expensive reagents, long reaction times, and low yields
In addition, these reactions are carried out in organic solvents at high temperatures, which do not meet the requirements of green chemistry, resulting in high costs

Method used

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  • Room temperature solvent-free synthesis of 3,4-dihydropyrimidine-2-ketone
  • Room temperature solvent-free synthesis of 3,4-dihydropyrimidine-2-ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In a 100mL round bottom flask, add 21.22g (0.2mol) benzaldehyde, 26.03g (0.2mol) ethyl acetoacetate, 18.02g (0.3mol) urea, 2.88g (0.015mol) citric acid, mix well, stir at room temperature for 1 hours, suction filtered, washed with ice water, washed with a small amount of 40% ethanol-aqueous solution, then washed with water, and dried and weighed the solid to obtain 49.94 g of product with a yield of 96.0%.

Embodiment 2

[0024] In a 100mL round bottom flask, add 21.22g (0.2mol) benzaldehyde, 20.03g (0.2mol) acetylacetone, 18.02g (0.3mol) urea, 3.84g (0.02mol) citric acid, mix well, stir at room temperature for 1.5 hours, Suction filtration, washing with ice water, washing with a small amount of 40% ethanol-aqueous solution, then washing with water, drying and weighing of the solid to obtain 44.89 g of the product with a yield of 97.6%.

Embodiment 3

[0026] In a 100mL round bottom flask, add 21.22g (0.2mol) benzaldehyde, 26.03g (0.2mol) ethyl acetoacetate, 18.02g (0.3mol) urea, 1.81g (0.02mol) oxalic acid, mix well, stir at room temperature for 1.5 hours , filtered with suction, washed with ice water, washed with a small amount of 40% ethanol-water solution, then washed with water, dried and weighed the solid to obtain 51.02 g of the product with a yield of 98.1%.

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Abstract

The present invention discloses a synthesis method of 3, 4-dihydro pyrimidine-2-alkone at the room temperature without a solvent. The synthesis method comprises the following steps: under the condition without a solvent, an aldehyde compound as shown in Formula (II), beta-dicarbonyl compound as shown in Formula (III) and a compound as shown in Formula (IV) are mixed for reaction with an acid catalyst at the room temperature, a TLC is used for examining the end point of the reaction, the filtered residue can be acquired through filtration after the reaction is completed, and the product as shown in Formula (I) can be acquired after the filter residue is washed and dried. The present invention has the advantages that the operation is simple, the yield rate of the reaction is high, the purity of the product is high, the process is conducive to the environmental protection, the product cost is low, and the present invention is suitable for industrial production.

Description

(1) Technical field [0001] The present invention relates to a synthetic method of 3,4-dihydropyrimidin-2-one. (2) Background technology [0002] 3,4-dihydropyrimidin-2-one and its derivatives are important pharmaceutical intermediates. Due to their unique structure and potential pharmacological properties, they have numerous biological activities and can be made into antihypertensive agents, calcium antagonists, Anti-allergic agent, also has antibacterial, antitumor, antiviral, anti-inflammatory and other effects. One of the most biologically active alkaloids is Batzeldine alkaloid, which can become a potential leading compound for the treatment of AIDS because of its ability to effectively inhibit the binding of HIV membrane protein gp-120 to human CD4 cells. Therefore, the synthesis of 3,4-dihydropyrimidone and its derivatives has attracted extensive attention. [0003] The earliest synthesis of this compound is to obtain 3,4-dihydropyrimidinone by heating and refluxing ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/36C07D239/40
Inventor 裴文王勤
Owner 山东兴安智慧科技有限公司
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