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Synthesis process, intermediate and pharmaceutical process of 2, 4, 5-triamino-6-hydroxypyrimidine

A technology of hydroxypyrimidine and synthesis process, applied in the direction of organic chemistry and the like, can solve problems such as high cost and no economic feasibility, and achieve the effects of reducing water consumption and wastewater output, great economic significance and environmental protection significance

Inactive Publication Date: 2021-08-06
山东晶原生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If organic solvents are used instead of water, the cost of dealing with residual solvents is also particularly high, and it is not economically feasible

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The 2-nitroso group of embodiment 1 liquid, the synthetic technique of 2-methyl cyanoacetate

[0028] Use the following reaction formula:

[0029] Methyl cyanoacetate + sodium nitrite = 2-nitroso, 2-methyl cyanoacetate.

[0030] That is, methyl cyanoacetate and sodium nitrite are used for nitrosation reaction.

[0031] In the process of nitrosation reaction, there is no limit to the reaction dropping method, the reaction container is not limited, the dropping speed is not limited, the dropping ratio is not limited, and the temperature is controlled at -20 ~ 100 ° C; in different dropping methods, the reactor , The addition rate can realize this step reaction, the drop ratio is 1:1 mole is the best, the temperature is 0-20°C is the best.

Embodiment 2

[0032] The 2-nitroso of embodiment 2 liquid, the synthetic technique of ethyl 2-cyanoacetate

[0033] Use the following reaction formula:

[0034] Ethyl cyanoacetate + sodium nitrite = 2-nitroso, 2-ethyl cyanoacetate.

[0035] That is, it is produced by nitrosation reaction of ethyl cyanoacetate and sodium nitrite.

[0036] In the process of nitrosation reaction, there is no limit to the reaction dropping method, the reaction vessel, the dropping speed, the dropping ratio, and the temperature is controlled at -20-100°C. This step reaction can be realized in different dropping methods, reactors, and dropping speeds. The best dropping ratio is 1:1 by mole, and the best temperature is 0-20°C.

Embodiment 3

[0037] Example 3 Synthesis process (1) of 2,4,5-triamino-6-hydroxypyrimidine

[0038] Use the following reaction formula:

[0039] 1) methyl cyanoacetate + sodium nitrite = 2-nitroso, 2-methyl cyanoacetate;

[0040] 2) 2-Nitroso, methyl 2-cyanoacetate + H 2 (Catalyst) = 2-amino, 2-cyanoacetic acid methyl ester;

[0041] 3) Free guanidine+2-amino, 2-cyanoacetic acid methyl ester=2,4,5-triamino-6-hydroxypyrimidine;

[0042] That is, first adopt the nitrosation method in Example 1 to synthesize 2-nitroso, methyl 2-cyanoacetate; then use liquid 2-nitroso, methyl 2-cyanoacetate to undergo pressurized catalytic hydrogenation reaction Generate 2-amino, methyl 2-cyanoacetate; for this catalytic hydrogenation step, noble metals such as nickel, palladium, platinum, rhodium can be selected as catalysts, and the concentration and form of the catalysts are not limited. The pressure during the catalytic reaction is 0.1-10Mpa, the time is 1-1000 minutes, the use of any form of reaction v...

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PUM

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Abstract

The invention discloses a synthesis process of 2, 4, 5-triamino-6-hydroxypyrimidine, which comprises the following steps: 1) carrying out pressurized catalytic hydrogenation reaction on liquid 2-nitroso and 2-methyl cyanoacetate / ethyl cyanoacetate to generate 2-amino and 2-cyanoacetic acid methyl ester / ethyl ester; (2) carrying out cyclization reaction on the 2-amino, 2-methyl cyanoacetate / ethyl cyanoacetate and free guanidine to generate 2, 4, 5-triamino-6-hydroxypyrimidine; wherein the liquid 2-nitroso and 2-methyl cyanoacetate / ethyl cyanoacetate in the step 1) are generated by carrying out nitrosation reaction on methyl cyanoacetate / ethyl cyanoacetate and sodium nitrite. The invention also discloses intermediates 2-nitroso and 2-methyl cyanoacetate in the synthesis process, a synthesis process of the intermediates, and a pharmaceutical process taking the 2, 4, 5-triamino-6-hydroxypyrimidine as an intermediate. According to the present invention, the liquid new compounds such as 2-nitroso and 2-methyl cyanoacetate / ethyl cyanoacetate are subjected to the catalytic hydrogenation reaction, such that the problems of large water consumption and large wastewater yield in the 2, 4, 5-triamino-6-hydroxypyrimidine synthesis process can be solved, and the great economic significance and the great environmental protection significance are provided.

Description

technical field [0001] The invention relates to the field of pharmacy, in particular to a synthesis process, an intermediate and a pharmacy process of 2,4,5-triamino-6-hydroxypyrimidine. Background technique [0002] 2,4,5-Triamino-6-hydroxypyrimidine is an important intermediate of vitamin folic acid and a series of high-efficiency and low-toxic antiviral drugs such as acyclovir and famciclovir. [0003] At present, 2,4,5-triamino-6-hydroxypyrimidine has been using the traditional synthetic route: [0004] (1) guanidine hydrochloride / guanidine nitrate+sodium methylate / methanol=free guanidine+methanol solution; [0005] (2) free guanidine+methyl cyanoacetate / ethyl cyanoacetate=2,4-diamino-6-hydroxypyrimidine; [0006] (3) 2,4-diamino-6-hydroxypyrimidine+sodium nitrite=2,4-diamino-5-nitroso-6-hydroxypyrimidine; [0007] (4) 2,4-diamino-5-nitroso-6-hydroxypyrimidine+H 2 (Catalyst) = 2,4,5-triamino-6-hydroxypyrimidine. [0008] But the synthetic route of above-mentioned 2,...

Claims

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Application Information

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IPC IPC(8): C07D239/50
CPCC07D239/50
Inventor 田雨
Owner 山东晶原生物技术有限公司
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