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Preparation method of 4-chloro-5-methylpyrimidine

A technology of methylpyrimidine and hydrazinopyrimidine, which is applied in the field of preparation of 4-chloro-5-methylpyrimidine, can solve problems such as complex operation, pulmonary fibrosis, and respiratory tract inflammation, and achieve simple operation, accelerated reaction process, The effect of short reaction steps

Active Publication Date: 2015-06-24
贵州威顿晶磷电子材料股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The process route for preparing 4-chloro-5-methylpyrimidine has many reaction steps, the operation is relatively complicated, and reflux operation is required for 16 hours, and the efficiency is low
Raney nickel is used as a catalyst in the reaction. After participating in the reaction, Raney nickel may still contain a large amount of hydrogen and should be destroyed in a ventilated place. Harmful gas will be produced when Raney nickel is burned; direct contact with Raney nickel may cause respiratory inflammation , can also cause eye and skin irritant damage, inhalation can lead to fibrosis of the nasal cavity and lungs, and is more harmful to the human body

Method used

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  • Preparation method of 4-chloro-5-methylpyrimidine
  • Preparation method of 4-chloro-5-methylpyrimidine
  • Preparation method of 4-chloro-5-methylpyrimidine

Examples

Experimental program
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Effect test

Embodiment 1

[0026] (1) Synthesis of 4-chloro-5-methyl-6-hydrazinopyrimidine

[0027] Add 82g of a mixed solution of methanol and isopropanol prepared in the same volume to the reactor, add 60g of hydrazine hydrate under room temperature stirring, add 51g of 4,6-dichloro-5-methylpyrimidine after stirring evenly, and heat up to 60°C React until the reaction is complete as detected by thin-layer chromatography, cool, filter with suction, wash the filter cake with 150 g of distilled water until it is colorless, and dry it to constant weight to obtain 46.89 g of white solid 4-chloro-5-methyl-6-hydrazinopyrimidine , and the yield was 94.5%.

[0028] (2) Synthesis of 4-chloro-5-methylpyrimidine

[0029] Add 94.7g ethanol in the reactor, and 50g of 4-chloro-5-methyl-6-hydrazinopyrimidine obtained in 120g distilled water and (1) are added in the reactor, add 110g mercuric oxide under stirring, reaction temperature Control at 20°C, react for 40 minutes, end the reaction, filter out the suspended ...

Embodiment 2

[0033] A preparation method of 4-chloro-5-methylpyrimidine, comprising the steps of:

[0034] (1) Synthesis of 4-chloro-5-methyl-6-hydrazinopyrimidine

[0035] Add 82g of isopropanol to the reactor, add 60g of hydrazine hydrate under stirring at room temperature, stir well, then add 53.4g of 4,6-dichloro-5-methylpyrimidine, heat up to 70°C and react until the reaction is complete as detected by thin-layer chromatography , cooled, filtered with suction, the filter cake was washed with 175g of distilled water until it was colorless, and dried to constant weight to obtain 50.55g of 4-chloro-5-methyl-6-hydrazinopyrimidine as a white solid with a yield of 97.3%.

[0036] (2) Synthesis of 4-chloro-5-methylpyrimidine

[0037] Add 119g ethanol in the reactor, join 50g of 4-chloro-5-methyl-6-hydrazine pyrimidine obtained in 150g distilled water and (1) in the reactor, add 110g mercuric oxide under stirring, the reaction temperature is controlled at 40°C, react for 35 minutes, end the...

Embodiment 3

[0041] A preparation method of 4-chloro-5-methylpyrimidine, comprising the steps of:

[0042] (1) Synthesis of 4-chloro-5-methyl-6-hydrazinopyrimidine

[0043] Add 105g of isopropanol to the reactor, add 60g of hydrazine hydrate under stirring at room temperature, add 54g of 4,6-dichloro-5-methylpyrimidine after stirring evenly, heat up to 80°C and react until the reaction is complete as detected by thin-layer chromatography. Cool, filter with suction, wash the filter cake with 180 g of distilled water until it is colorless, and dry it to constant weight to obtain 52.12 g of 4-chloro-5-methyl-6-hydrazinopyrimidine as a white solid with a yield of 99.2%.

[0044] (2) Synthesis of 4-chloro-5-methylpyrimidine

[0045] Add 119g methanol in the reactor, join 50g of 4-chloro-5-methyl-6-hydrazine pyrimidine obtained in 150g distilled water and (1) in the reactor, add 135g mercuric oxide under stirring, the reaction temperature is controlled at 60°C, react for 30 minutes, end the re...

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Abstract

The invention discloses a preparation method of 4-chloro-5-methylpyrimidine, which comprises the following steps: adding solvent A into the reactor, slowly adding hydrazine hydrate under stirring at room temperature, and then adding hydrazine hydrate with a mass of 0.85- 0.92 times the amount of 4,6-dichloro-5-methylpyrimidine, heated up to 60°C-80°C and reacted until the reaction was detected by thin-layer chromatography, cooled, suction filtered, and the filter cake was washed with 150-180 parts by mass of distilled water, Dry to constant weight to obtain 4-chloro-5-methyl-6-hydrazinopyrimidine; add B solvent to the reactor, then add distilled water and 4-chloro-5-methyl-6-hydrazinopyrimidine, stir Add 2.2-2.8 times the mass of mercuric oxide of 4-chloro-5-methyl-6-hydrazinopyrimidine to react, control the reaction temperature at 20-60°C, react for 30-40 minutes, filter with suction, and wash with petroleum ether filter cake, and the obtained filtrate was extracted with petroleum ether, and the petroleum ether layer was dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the product 4-chloro-5-methylpyrimidine. The invention has short reaction steps, high product yield, simple operation, low cost, safety and environmental protection.

Description

technical field [0001] The invention belongs to the technical field of chemistry and relates to a preparation method of 4-chloro-5-methylpyrimidine. Background technique [0002] 4-Chloro-5-methylpyrimidine is an important intermediate in drug synthesis and can be used in the synthesis of benzodiazepines, capsaicin receptor (VR1) and TRPV1. The preparation method of 4-chloro-5-methylpyrimidine at present, relevant literature report is as follows: [0003] The synthetic route of 4-chloro-5-methylpyrimidine disclosed in "Organic Chemistry" (1984, 49 (2): 296-300, David L. Coffen) is as follows: [0004] [0005] The process route for synthesizing 4-chloro-5-methylpyrimidine has relatively long reaction steps, each reaction stage requires more reaction steps, and the operation is relatively complicated. [0006] PCT Int.Appl., 2010041054, 2010, the process route for preparing 4-chloro-5-methylpyrimidine disclosed by McDonald (Madonna), Edward (Edward) et al. is as follows:...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/30
Inventor 赵春深蒋飚刘涛吴郁林李飞肖文斌赵顺郭之军
Owner 贵州威顿晶磷电子材料股份有限公司