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Process for synthesizing 3,4-dihydropyrimidine-2-keto

A technology of dihydropyrimidine and synthesis method, applied in 3 fields, can solve the problems of long reaction time, expensive reagents, low yield and the like, and achieves the effects of low production cost, good product purity and reduced production cost

Inactive Publication Date: 2009-06-24
无棣鑫岳化工集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned measures have all improved the conversion rate to a certain extent, but there are still defects, such as expensive reagents, long reaction time, too strong acidity, low yield, etc.
In addition, these reactions are carried out under the action of organic solvents and catalysts, resulting in high costs

Method used

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  • Process for synthesizing 3,4-dihydropyrimidine-2-keto
  • Process for synthesizing 3,4-dihydropyrimidine-2-keto
  • Process for synthesizing 3,4-dihydropyrimidine-2-keto

Examples

Experimental program
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Effect test

Embodiment 1

[0024] In a 100mL round bottom flask, add 21.22g (0.2mol) benzaldehyde, 20.03g (0.2mol) acetylacetone, 18.02g (0.3mol) urea, mix well, stir and heat at 110°C for 1.5 hours, cool, suction filter, filter The cake was washed with ice water, then washed with a small amount of 40% ethanol-water solution by volume, and then washed with water, and the solid was dried and weighed to obtain 44.89 g of the product, with a yield of 97.6%.

Embodiment 2

[0026] In a 100mL round bottom flask, add 21.22g (0.2mol) benzaldehyde, 20.03g (0.2mol) acetylacetone, 18.02g (0.3mol) urea, mix well, stir and heat at 80°C for 1.5 hours, cool, suction filter, filter The cake was washed with ice water, then with a small amount of 40% ethanol-water solution by volume, and then with water, and the solid was weighed dry to obtain 42.77 g of the product, with a yield of 93%.

Embodiment 3

[0028] In a 100mL round bottom flask, add 21.22g (0.2mol) benzaldehyde, 26.03g (0.2mol) ethyl acetoacetate, 18.02g (0.3mol) urea, mix well, stir and heat at 150°C for 1.5 hours, cool, and filter with suction , the filter cake was washed with ice water, then washed with a small amount of 40% volume concentration ethanol-water solution, and then washed with water, and the solid was weighed after drying to obtain 49.94 g of the product, with a yield of 96.0%.

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Abstract

The invention discloses a synthetic method of 3,4-dihydropyrimidin-2-one. In a condition without solvent and catalyst, an aldehyde compound of formula (II), a beta-dicarbonyl compound of formula (III) and an urea compound of formula (IV) are taken as raw materials, stirred and heated for 0.5-10h reaction at the reaction temperature of 80-150 DEG C, reaction solution is separated to obtain the 3,4-dihydropyrimidin-2-one of formula (I). In the whole process, only a little ethanol aqueous solution is used for washing, catalyst is not needed, a 'one pot synthesis' is used for preparation, and the operation is simple, thus avoiding the disadvantages of high energy consumption, serious pollution, high toxicity, inflammable and explosive properties and the like which are caused by the use of the solvent, and the method is environmentally friendly and suitable for the though of the green chemistry, and helps reduces the production cost.

Description

(1) Technical field [0001] The invention relates to a synthesis 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, Antiallergic agent, also has antibacterial, antitumor, antiviral, anti-inflammatory and other effects. Among them, the most biologically active is the Batzelladine alkaloid, because it can effectively inhibit the combination of HIV membrane protein gp-120 and human CD4 cells, it can become a very potential lead compound for the treatment of AIDS. Therefore, the synthesis of 3,4-dihydropyrimidin-2-one and its derivatives has attracted widespread attention. [0003] The earliest synthesis of this compound is to obtain 3,4-dihydropyrimidin-2-one by heating and refluxing ethyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/22
Inventor 裴文王勤王海滨
Owner 无棣鑫岳化工集团有限公司
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