Method for synthesizing 2-methyl-4-amino-5-formamide methyl pyrimidine

A technology of formamide methyl pyrimidine and synthesis method, which is applied in the field of compound synthesis and can solve the problems of high construction cost and maintenance cost, residual end product and high cost

Active Publication Date: 2019-11-15
XIAMEN KINGDOMWAY VI TAMIN INC +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The current process used to synthesize enol sodium salt is high-pressure reaction, the reaction pressure is in the range of 3-6MPa, and the product is solid. In the large-scale production process, the cost of large-scale high-pressure equipment and maintenance costs are high, and there is a certain risk.
[0005] Among them, the patent application US4716243A uses enol sodium salt as raw material, forms enamine with o-chloroaniline, and then reacts with acetamidine to obtain the product. , there is a risk of end product residue, and the cost of recycling o-chloroaniline is relatively high
Patent application CN103420918A adopts enol sodium salt to directly react with acetamidine, and under the action of Lewis acid such as zinc chloride, directly obtains the product formylpyrimidine, and the highest yield can reach 74%, but uses Lewis acid such as zinc chloride as a catalyst , the amount of which is about 0.15-0.3 equivalents, the cost is high, and in the post-treatment process, the by-product zinc hydroxide precipitates, and the separation is difficult in the industrial production process

Method used

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  • Method for synthesizing 2-methyl-4-amino-5-formamide methyl pyrimidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 174g methyl formate (content 97.0%, 2.81mol) in the three-necked bottle, add 40g beta-aminopropionitrile (content 98.5%, 0.56mol) wherein, stir; Add 75.92g liquid methanol in another three-necked bottle Sodium (content 20%, 0.28mol); Setting pipeline reactor temperature is 55 ℃, opens feed pump, and above-mentioned two strands of materials are fed simultaneously, feed rate is 21.4g / min and 7.59g / min, reactor The residence time in medium is about 3min. After the reaction is stable, receive and discharge the material for 5min (i.e., take half of the product for the subsequent reaction, the following examples are the same), the feed liquid is cooled to room temperature, neutralized to neutral with acetic acid, and then decompressed The solvent was removed, 300 mL of toluene was added thereto, washed with water twice, and dried to obtain a toluene solution of 2-formyl-3-formylamino-propionitrile, which was set aside.

[0024] In the three-necked flask, 49.3g of sodium e...

Embodiment 2

[0032] Add 104.40g methyl formate (content 97.0%, 1.69mol) in the three-necked bottle, add 40g beta-aminopropionitrile (content 98.5%, 0.56mol) to it, stir; Add 45.55g liquid to another three-necked bottle Sodium methylate (content 20%, 0.16mol); Setting pipeline reactor temperature is 50 ℃, opens feed pump, and above-mentioned two strands of material are fed simultaneously, and feed rate is 14.44g / min and 4.55g / min, and reaction The residence time in the container is about 5 minutes. After the reaction is stable, receive and discharge the material for 5 minutes, cool the material liquid to room temperature, neutralize it with glacial acetic acid to neutrality, then remove the solvent under reduced pressure, add 300 mL of toluene to it, wash twice with water, and dry The toluene solution of 2-formyl-3-formylamino-propionitrile was obtained and set aside.

[0033]In the three-necked flask, 39.44g of sodium ethylate (content 97%, 0.56mol) was dissolved in 300mL of ethanol, after...

Embodiment 3

[0035] Add 278.40g methyl formate (content 97.0%, 4.50mol) in the three-necked bottle, add 40g beta-aminopropionitrile (content 98.5%, 0.56mol) to it, stir well; Add 151.83g liquid in another three-necked bottle Sodium methylate (content 20%, 0.56mol); Setting pipeline reactor temperature is 50 ℃, opens feed pump, and above-mentioned two strands of material are fed simultaneously, and feed rate is 31.84g / min and 15.18g / min, and reaction The residence time in the container is about 4 minutes. After the reaction is stable, receive and discharge the material for 5 minutes, cool the material liquid to room temperature, neutralize it with glacial acetic acid to neutrality, then remove the solvent under reduced pressure, add 300 mL of toluene to it, wash twice with water, and dry The toluene solution of 2-formyl-3-formylamino-propionitrile was obtained and set aside.

[0036] In the three-necked flask, 69.01g of sodium ethylate (content 97%, 0.98mol) was dissolved in 300mL of ethano...

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Abstract

The invention discloses a method for synthesizing 2-methyl-4-amino-5-formamide methyl pyrimidine. The method comprises the following steps: conveying an organic ester solvent solution with beta-aminopropionitrile and an organic alcohol solution with sodium alcoholate into a pipeline reactor, performing a continuous reaction, discharging the materials, performing cooling, performing neutralizationto neutral, performing vacuum recycling on a solvent, continuously adding methylbenzene, and performing water washing so as to obtain a methylbenzene solution of 2-formyl-3-formyl amino-propionitrile;adding acetamidine hydrochloride into the organic alcohol solution with sodium alcoholate, performing filtration after addition, collecting filtrate, performing heating, putting the methylbenzene solution of 2-formyl-3-formyl amino-propionitrile; and adding acetamidine hydrochloride into the filtrate, under a vacuum condition, evaporating out the solvent and adding an alcohol of a corresponding volume at the same time, stopping the reaction when a solution of a volume equal to that of the organic alcohol solution with the sodium alcoholate is evaporated out, performing neutralization to neutral, performing vacuum crystallization, performing filtering, and performing drying, so as to obtain the compound. The method is simple, gentle in reaction condition, low in reaction equipment requirement, low in cost and high in yield.

Description

technical field [0001] The invention relates to the field of compound synthesis methods, in particular to a synthesis method of 2-methyl-4-amino-5-carboxamidomethylpyrimidine. Background technique [0002] 2-Methyl-4-amino-5-carboxamidomethylpyrimidine is an important intermediate in the synthesis of vitamin B1, and its molecular formula is as follows: [0003] [0004] The existing domestic main synthetic techniques all use β-aminopropionitrile as the raw material, undergo high-pressure reaction to obtain enol sodium salt, and then carry out cyclization reaction with acetamidine to obtain 2-methyl-4-amino-5-carboxamidomethylpyrimidine . The current process used to synthesize enol sodium salt is high-pressure reaction, the reaction pressure is in the range of 3-6MPa, and the product is solid. In the large-scale production process, the cost of large-scale high-pressure equipment and maintenance costs are high, and there is a certain risk. . [0005] Among them, the pate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/42
CPCC07D239/42
Inventor 马瑞达魏高宁戴剑坤汤镇伟刘敏
Owner XIAMEN KINGDOMWAY VI TAMIN INC
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