Preparation method of 2-methoxy-5-amino-4-methylpyrimidine

A technology of methyl pyrimidine and methoxy group, applied in the field of fine chemical intermediates, achieves the effect of simple synthesis process and convenient operation

Pending Publication Date: 2020-06-09
DALIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the basis of extensive literature research, there is no "one-step" preparation of 2-methoxy-5-amino-4 from 2-methoxy-5-nitro-4-methyl-6-chloropyrimidine -the method of methyl pyrimidine, thus need to develop a kind of synthetic route of preparing this compound

Method used

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  • Preparation method of 2-methoxy-5-amino-4-methylpyrimidine
  • Preparation method of 2-methoxy-5-amino-4-methylpyrimidine
  • Preparation method of 2-methoxy-5-amino-4-methylpyrimidine

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Embodiment 1

[0016] The present embodiment is the preparation method of 2-methoxy-5-amino-4-methylpyrimidine, according to the following reaction formula:

[0017]

[0018] The specific experimental process is as follows:

[0019] Add 2-methoxyl-5-nitro-4-methyl-6-chloropyrimidine 8g (0.04mol, 1.0eq) into the autoclave, add methanol 80ml, nickel 0.4g, triethylamine 4g (0.04mol, 1.0eq), at 30°C and 2.0MPa, hydrogen gas was introduced, stirred for 2h, the reaction was completed, filtered, the filtrate was concentrated, 20ml of water was added, extracted with EA, dried, and frozen to obtain the product 2-methoxy-5-amino - 4.1 g of 4-methylpyrimidine, GC: 98%, yield 74%.

Embodiment 2

[0021] The present embodiment is the preparation method of 2-methoxy-5-amino-4-methylpyrimidine, according to the following reaction formula:

[0022]

[0023] The specific experimental process is as follows:

[0024] Add 2-methoxyl-5-nitro-4-methyl-6-chloropyrimidine 8g (0.04mol, 1.0eq) into the autoclave, add methanol 80ml, nickel 0.4g, triethylamine 4g (0.04mol, 1.0eq), flow hydrogen at 30°C and 2.0MPa, stir for 5h, after the reaction is complete, filter, concentrate the filtrate, add 20ml of water, heat extraction with EA, dry, and freeze to obtain the product 2-methoxy-5-amino - 4.3 g of 4-methylpyrimidine, GC: 98%, yield 78%.

Embodiment 3

[0026] The present embodiment is the preparation method of 2-methoxy-5-amino-4-methylpyrimidine, according to the following reaction formula:

[0027]

[0028] The specific experimental process is as follows:

[0029] Add 2-methoxy-5-nitro-4-methyl-6-chloropyrimidine 8g (0.04mol, 1.0eq) in the autoclave, add acetonitrile 80ml, nickel 0.4g, triethylamine 4g (0.04mol, 1.0eq), flow hydrogen at 30°C and 2.0MPa, stir for 5h, after the reaction is complete, filter, concentrate the filtrate, add 20ml of water, heat extraction with EA, dry, and freeze to obtain the product 2-methoxy-5-amino - 3.9 g of 4-methylpyrimidine, GC: 98%, yield 71%.

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Abstract

The invention discloses a preparation method of 2-methoxy-5-amino-4-methylpyrimidine, and belongs to the technical field of organic chemistry. The method comprises the following steps: carrying out ahydrogenation reaction by taking 2-methoxy-5-nitro-4-methyl-6-chloropyrimidine as a raw material, methanol as a solvent, triethylamine as an acid-binding agent and nickel as a catalyst to generate a mixture of 2-methoxy-5-amino-4-methylpyrimidine and other impurities, filtering, extracting, drying, and freezing to obtain a pure product 2-methoxy-5-amino-4-methylpyrimidine with the yield of 71-86%.According to the preparation method, the defects of the existing synthesis process are overcome, and a new method for synthesizing 2-methoxy-5-amino-4-methylpyrimidine is provided.

Description

technical field [0001] The invention relates to a "one-pot method" method for preparing 2-methoxy-5-amino-4-methylpyrimidine, which belongs to the field of fine chemical intermediates. Background technique [0002] 2-Methoxy-5-amino-4-methylpyrimidine is an important heterocyclic compound, which has a wide range of biological activities and pharmacological effects in many aspects, such as: antitumor, antibacterial, antimalarial, insecticide, etc. On the one hand, due to its special properties, it can also be used in the synthesis of chemical intermediates and biological intermediates. [0003] In the existing methods for synthesizing 2-methoxy-5-amino-4-methylpyrimidine, the reaction conditions are harsh. On the basis of extensive literature research, there is no "one-step" preparation of 2-methoxy-5-amino-4 from 2-methoxy-5-nitro-4-methyl-6-chloropyrimidine -The method of methyl pyrimidine, thus need to develop a kind of synthetic route of preparing this compound. Conte...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/47
CPCC07D239/47
Inventor 王爱玲王肖肖崔颖娜王帆郑学仿
Owner DALIAN UNIV
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