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Preparation method of 4, 6-dihydroxypyrimidine

A technology of dihydroxypyrimidine and malonate, applied in the direction of organic chemistry, can solve problems such as shortages, achieve the effects of reducing dosage, exerting economic benefits, and improving reaction yield

Pending Publication Date: 2022-07-01
CAC NANTONG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When this method is applied to the continuous industrial production of 4,6-dihydroxypyrimidine, the content of organic by-products or impurities in the generated wastewater is still high, and wastewater treatment is still difficult. Facing the increasing environmental protection requirements of today's society and industries Higher expectations for greener chemistry, such synthetic methods still have deficiencies

Method used

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  • Preparation method of 4, 6-dihydroxypyrimidine
  • Preparation method of 4, 6-dihydroxypyrimidine

Examples

Experimental program
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Effect test

Embodiment 1

[0038] In this embodiment, 4,6-dihydroxypyrimidine is prepared by the following method, which specifically includes the following steps:

[0039] Set up a four-necked flask reaction device equipped with a constant pressure dropping funnel, stirring paddle, thermometer and reflux condenser, weigh 81.03g (0.450mol) (content 30%) of sodium methoxide / methanol solution, 0.43g (0.0023mol) ( content 97%) tetramethylammonium hydroxide pentahydrate, stir evenly, heat up to 60 ° C, start to dropwise add 30.03g (0.225mol) (content 99%) dimethyl malonate and 25.57g (0.562mol) (content 99%) formamide mixture, the dropwise addition time is 45min. After the dropwise addition, the reaction was incubated at 60 °C for 3 h. Subsequently, methanol was recovered by distillation to dryness. After the residual solid was dissolved in water, it was acidified to pH 2.53 with 30% hydrochloric acid at 25°C, filtered, washed with water, and dried to obtain 24.06 g of 4,6-dihydroxypyrimidine with a conten...

Embodiment 2

[0041] In this embodiment, 4,6-dihydroxypyrimidine is prepared by the following method, which specifically includes the following steps:

[0042]Set up a four-necked flask reaction device equipped with a constant pressure dropping funnel, stirring paddle, thermometer and reflux condenser, weigh 81.03g (0.450mol) (content 30%) of sodium methoxide / methanol solution, 0.24g (0.0013mol) ( content 97%) tetramethylammonium hydroxide pentahydrate, stir evenly, heat up to 65 ℃, start to dropwise add 30.03g (0.225mol) (content 99%) dimethyl malonate and 25.57g (0.562mol) (content 99%) formamide mixture, the dropwise addition time is 1h. After the dropwise addition, the reaction was incubated at 65°C for 2h. Subsequently, methanol was recovered by distillation to dryness. After the residual solid was dissolved in water, it was acidified to pH 2.75 with 30% hydrochloric acid at 23°C, filtered, washed with water, and dried to obtain 23.88 g of 4,6-dihydroxypyrimidine with a content of 98....

Embodiment 3

[0044] In this embodiment, 4,6-dihydroxypyrimidine is prepared by the following method, which specifically includes the following steps:

[0045] Set up a four-necked flask reaction device equipped with a constant pressure dropping funnel, stirring paddle, thermometer and reflux condenser, and weigh 60.77g (0.450mol) (content 40%) sodium methoxide / methanol solution, 0.64g (0.0034mol) ( content 97%) tetramethylammonium hydroxide pentahydrate, stir evenly, heat up to 65 ℃, start to dropwise add 30.03g (0.225mol) (content 99%) dimethyl malonate and 28.66g (0.630mol) (content 99%) formamide mixture, the dropwise addition time is 1h. After the dropwise addition, the reaction was incubated at 65°C for 2h. Subsequently, methanol was recovered by distillation to dryness. After the residual solid was dissolved in water, it was acidified to pH 2.46 with 30% hydrochloric acid at 25°C, filtered, washed with water, and dried to obtain 24.16 g of 4,6-dihydroxypyrimidine with a content of 9...

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Abstract

The invention provides a preparation method of 4, 6-dihydroxypyrimidine, which comprises the following steps: dropwise adding a mixed solution of malonate and formamide into an alkali metal alcoholate / solvent containing a catalyst, and carrying out heat preservation reaction after dropwise adding is completed. And after the reaction is finished, evaporating the solvent to dryness, adding water to dissolve until the solution is clear, acidifying until the pH is 2-3, filtering, washing with water, and drying to obtain the 4, 6-dihydroxypyrimidine. The method utilizes the catalyst to catalyze the reaction, improves the reaction yield, has high atom economy, reduces the use amount of raw materials, reduces the generation of salt-containing wastewater, and relieves the environmental protection pressure.

Description

Technical field [0001] The invention belongs to the technical field of organic chemistry, and specifically relates to a preparation method of 4,6-dihydroxypyrimidine. Background technique [0002] 4,6-Dihydroxypyrimidine is an important fine chemical raw material or organic synthesis intermediate. It is widely used in medicine, pesticides and fungicides. For example, it is used in the pharmaceutical industry to produce sulfonamides. Intermediates for toxin, vitamin B4, anti-tumor drugs and auxiliary drugs; used as intermediates in the preparation of methoxyacrylate fungicides azoxystrobin in pesticides, etc. [0003] There are mainly two ways to prepare 4,6-dihydroxypyrimidine in the prior art: (1) using malonamide and esters (such as ethyl formate or triethyl orthoformate, etc.) as raw materials to prepare 4,6-dihydroxypyrimidine. -Dihydroxypyrimidine; (2) Use malonate (such as dimethyl malonate, diethyl malonate, etc.) and formamide or formamidine hydrochloride as raw mat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/54
CPCC07D239/54
Inventor 陈亮王雅冬王海水
Owner CAC NANTONG CHEM
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