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Preparation method of 2-chloro trifluoromethyl pyrimidine compound

A technology of chlorotrifluoromethylpyrimidine and trifluoromethylpyrimidine, applied in the field of organic synthesis, can solve the problems of improving yield, many by-products, low yield and the like, and achieves easy operation, low cost and high yield. Effect

Active Publication Date: 2015-04-22
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

[0004] (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
[0005] (2) Because the product has alcohol, the solvent itself inhibits the balance of the reaction
[0006] (3) second step chlorination adopts thionyl chloride and DMF to make solvent, and this method has many by-products, and yield is low

Method used

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  • Preparation method of 2-chloro trifluoromethyl pyrimidine compound
  • Preparation method of 2-chloro trifluoromethyl pyrimidine compound
  • Preparation method of 2-chloro trifluoromethyl pyrimidine compound

Examples

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Effect test

Embodiment 1

[0030] Example 1 Synthesis of 2-chloro-4-trifluoromethylpyrimidine (CAS33034-67-2)

[0031]

[0032] Trifluoroacetylacetaldehyde (14.8 grams, 0.106mol), urea (7.6 grams, 0.127mol), sodium ethylate (28.8 grams, 0.424mol) were added to the mixed solvent of 120ml toluene and 40ml ethanol, and the reaction apparatus was added Trap. Raise the reaction temperature from normal temperature to 120°C to 130°C and reflux for 12 hours. During the reaction, use a water separator to separate water from oil to remove water. 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 the crude product, which was washed with petroleum ether to obtain 15.7 g of 2-hydroxy-4-trifluoromethylpyrimidine, with a yield of 90.3%.

[0033] 2-Hydroxy-4-trifluoromethylpyrimidine (15.7 g, 0.096 mol) was added to acetonitrile (120 ml), ...

Embodiment 2

[0036] Example 2 2,4-dichloro-6-trifluoromethylpyrimidine (CAS16097-64-6)

[0037]

[0038] Ethyl trifluoroacetylacetate (16.8 grams, 0.091mol), urea (6.5 grams, 0.109mol), sodium ethylate (24.7 grams, 0.364mol) were added to a mixed solvent composed 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 and reflux for 12 hours. During the reaction, use a water separator to separate water from oil to remove water. The reaction solvent was spin-dried, adjusted to neutrality by adding 10% hydrochloric acid, and extracted three times with 80 ml of ethyl acetate. The ethyl acetate phases were combined, dried, filtered and spin-dried to obtain the crude product, which was washed with petroleum ether to obtain 15.2 g of 2,4-dihydroxy-6-trifluoromethylpyrimidine, with a yield of 92.8%.

[0039] 2,4-dihydroxy-6-trifluoromethylpyrimidine (15.7 g, 0.087 mol, 1 eq) was added to aceto...

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Abstract

The invention relates to the field of organic synthesis and discloses a preparation method of an intermediate 2-chloro trifluoromethyl pyrimidine compound. The method includes: using urea and trifluoroacetyl derivatives as raw meterials, and performing reflux reaction of alkali serving as catalyst with hydrocarbon and alcohol mixture serving as solvent; mixing an obtained 2-hydroxy trifluoromethyl pyrimidine compound with phosphorus oxychloride and acetonitrile for reaction for 2-24 hours at the temperature of 80-150 DEG C; and removing the solvent, adding water prior to alkalization, and extracting by organic solvent. The method is high in yield which can be more than 80%, low in cost and easy for industrialization.

Description

technical field [0001] The invention relates to the field of organic synthesis, and relates to a method for synthesizing intermediate pyrimidine compounds, especially a chlorotrifluoromethylpyrimidine compound, specifically a preparation method for 2-chlorotrifluoromethylpyrimidine compound. 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 trifluoromethy...

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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