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Preparation method of 4-chloro-6-trifluoromethylpyrimidine type compound

A technology of trifluoromethylpyrimidine and compound, applied in the field of organic synthesis, can solve the problems of many by-products, increase yield, low yield and the like, and achieve the effects of easy operation, low cost and high yield

Active Publication Date: 2015-07-01
上海泰坦科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] (1) A single solvent methanol is used, and the maximum temperature is limited to about 80°C, which is not conducive to increasing the yield by increasing the temperature
[0004] (2) Because the product has alcohol, the solvent itself inhibits the balance of the reaction
[0005] (3) In the second step of chlorination, thionyl chloride and DMF are used as solvents. This method has many by-products and low yield

Method used

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  • Preparation method of 4-chloro-6-trifluoromethylpyrimidine type compound
  • Preparation method of 4-chloro-6-trifluoromethylpyrimidine type compound
  • Preparation method of 4-chloro-6-trifluoromethylpyrimidine type compound

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Example 1 Synthesis of 4-chloro-6-trifluoromethylpyrimidine (CAS 37552-81-1)

[0027]

[0028] Add ethyl trifluoroacetylacetate (15.6 g, 0.085 mol), methyl ether hydrochloride (8.2 g, 0.102 mol), sodium ethoxide (23.1 g, 0.341 mol), into a mixed solvent consisting of 120 ml of toluene and 40 ml of ethanol , and the reaction device plus water separator. Raise the reaction temperature from normal temperature to 120°C-130°C and reflux for 12 hours. The reaction solvent was spin-dried, adjusted to neutrality (pH=6.5-7.5) by adding 10% hydrochloric acid, and extracted three times with 50 ml of ethyl acetate. The ethyl acetate phases were combined, dried, filtered and spin-dried to obtain a crude product; washed with petroleum ether to obtain 13.1 g of 4-hydroxy-6-trifluoromethylpyrimidine, with a yield of 93.6%.

[0029] 4-Hydroxy-6-trifluoromethylpyrimidine (13.1 g, 0.080 mol) was added to acetonitrile (120 ml), and POCl was added under room temperature and stirring 3...

Embodiment 2

[0032] Example 2 Synthesis of 4-chloro-2-methyl-6-trifluoromethylpyrimidine (CAS 5993-98-6)

[0033]

[0034] Ethyl trifluoroacetylacetate (12.3 grams, 0.067mol), diethyl ether hydrochloride (7.5 grams, 0.080mol), sodium ethylate (18.2 grams, 0.267mol) were added to a mixed solvent of 120ml toluene and 40ml ethanol, and the reaction apparatus Add water separator. Raise the reaction temperature from normal temperature to 120°C to 130°C, reflux for 12 hours, and use a water separator to separate and remove water during the reaction. The reaction solvent was spin-dried, adjusted to neutrality by adding 10% hydrochloric acid, and extracted three times with 50 ml of ethyl acetate. The ethyl acetate phases were combined, dried, filtered and spin-dried to obtain a crude product, which was washed with petroleum ether to obtain 11.4 g of 4-hydroxy-2-methyl-6-trifluoromethylpyrimidine with a yield of 95.7%.

[0035] 4-Hydroxy-6-trifluoromethylpyrimidine (11.4 g, 0.064 mol) was adde...

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Abstract

The invention relates to the field of organic synthesis and discloses a preparation method of an intermediate, namely a 4-chloro-6-trifluoromethylpyrimidine type compound. The preparation method comprises the following steps of: taking trifluoroacetyl ethyl acetate and ether hydrochloride as raw materials, using a base catalyst to perform solvent reflux reaction with a hydrocarbon and alcohol mixture; mixing an obtained 4-hydroxy-6-trifluoromethylpyrimidine type compound with phosphorus oxychloride and acetonitrile, and reacting for 2-24 hours at the temperature of 80-150 DEG C; and removing a solvent, adding water, alkalinizing and extracting with an organic solvent. According to the method disclosed by the invention, the yield is high and can be more than 80%, the cost is lower, and the industrialization is easy.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing intermediate pyrimidine compounds, especially a method for preparing 4-chloro-6-trifluoromethylpyrimidine compounds. Background technique [0002] Pyrimidine compounds occupy a very important position in pesticide and pharmaceutical research because of their simple structure and spectral drug activity. Drugs containing pyrimidine structure have good therapeutic effects in anti-cancer, anti-cardiovascular and cerebrovascular diseases, anti-microbial infection, etc. Many pesticides such as fungicides and insecticides also contain pyrimidine ring structure. Therefore, the development of intermediates containing pyrimidine structures has attracted more and more attention. And trifluoromethyl because of its strong electronegativity, high stability and good fat-solubility, the introduction of trifluoromethyl often makes the character of compound, especially p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/30
Inventor 谢应波张庆张华姚为建
Owner 上海泰坦科技股份有限公司
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