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Synthesis method of 2-hydroxymethyl-5-trifluoromethylpyrimidine

A technology for the synthesis of trifluoromethylpyrimidine and its synthesis method, which is applied in the field of synthesis of 2-hydroxymethyl-5-trifluoromethylpyrimidine, and can solve the industrial synthesis method of 2-hydroxymethyl-5-trifluoromethylpyrimidine There are no public reports and other problems, and the effect of cheap raw materials, unique reaction circuit and mild reaction conditions is achieved

Inactive Publication Date: 2019-07-09
上海吉奉生物科技有限公司
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Problems solved by technology

[0004] So far, there is no public report on the industrial synthesis method of 2-hydroxymethyl-5-trifluoromethylpyrimidine

Method used

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  • Synthesis method of 2-hydroxymethyl-5-trifluoromethylpyrimidine

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Embodiment Construction

[0010] step 1:

[0011] Add chloromethyl pivalate (40 g, 266 mmol) and acetonitrile (80 mL) to a 250 mL single-necked bottle, slowly add anhydrous sodium iodide (72 g, 480 mmol), under argon protection, room temperature ( about 25°C) to react overnight. Add water (400 mL) and dichloromethane (400 mL), stir for 5 min, and separate the layers. The organic phase is washed with 2% sodium thiosulfate (200 mL), dried over anhydrous sodium sulfate, and spin-dried ( below 40°C). Vacuum distillation (oil temperature 50°C) gave a colorless liquid, Compound 1 (55 g, 227 mmol, 85%).

[0012] Step 2:

[0013] Under the protection of argon, cool down in ice water, add zinc powder (27.2 g, 0.42 mol) and anhydrous tetrahydrofuran (120 mL) into a 500 mL three-necked flask, stir, add 10 drops of 1,2-dibromoethane, trimethyl Chlorosilane 10 drops, stirred for 5 minutes. Add the tetrahydrofuran solution (60 mL) of compound 1 (51.5 g, 0.21 mol) dropwise. After adding about 1 / 5 of the volume, ...

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Abstract

The invention relates to a synthesis method of 2-hydroxymethyl-5-trifluoromethylpyrimidine, which mainly solves the problems of lack of industrialized synthesis of 2-hydroxymethyl-5-trifluoromethylpyrimidine. The synthetic method of that invention comprises the following step: allowing chloromethyl pivalate to react with sodium iodide in acetonitrile to form compound 1 iodomethyl pivalate; allowing the iodomethyl pivalate to react with zinc powder in tetrahydrofuran solution to form compound 2 pivaloyl oxymethyl zinc iodide; allowing 2-chlorine-5-trifluoromethylpyrimidine to react with the compound 2 pivaloyl oxymethyl zinc iodide in the tetrahydrofuran solution to produce compound 3 under catalysis of tetrakis(triphenylphosphine)palladium; allowing the compound 3 to react with sodium methoxide to form target compound 4 in a methanol solution. As a pharmaceutical intermediate, 2-hydroxymethyl-5-trifluoromethylpyrimidine can be used in the field of chemical pharmaceuticals for the treatment of South American trypanosomiasis and African animal trypanosomiasis.

Description

technical field [0001] The present invention relates to a synthesis method of 2-hydroxymethyl-5-trifluoromethylpyrimidine (CAS: 944905-41-3). Background technique [0002] The protozoan parasite, Trypanosoma cruzi, causes Chagas disease (Chagas disease) in many Latin American countries, and in Africa, animal trypanosomiasis (AAT). In 2017, Tsutomu AKAMA reported the research on the treatment of trypanosomiasis in the field of chemical pharmaceuticals in the form of a patent (WO2017 / 195069 A1). As a pharmaceutical intermediate, 2-hydroxymethyl-5-trifluoromethylpyrimidine was used to synthesize the target compound 6-236, its synthesis method is as follows: [0003] [0004] So far, there is no public report on the industrial synthesis method of 2-hydroxymethyl-5-trifluoromethylpyrimidine. Contents of the invention [0005] The main purpose of the present invention is to provide a kind of synthetic method of 2-hydroxymethyl-5-trifluoromethylpyrimidine. The method mainly...

Claims

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Application Information

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IPC IPC(8): C07D239/26
CPCC07D239/26
Inventor 徐红岩马敬祥
Owner 上海吉奉生物科技有限公司
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