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Synthetic method of 7-tert-butyl 3-ethyl 8-methyl-5,6 dihydrotriazolopyrazine 3,7(8H) phthalate ester

A technology of dicarboxylate and methylpyrazine, applied to the production of 7-tert-butyl 3-ethyl 8-methyl 5,6 dihydrotriazolopyrazine 3,7(8H) dicarboxylate In the field of synthesis, achieve the effect of reasonable reaction process design and cost-saving synthesis

Inactive Publication Date: 2018-05-15
WUXI APPTEC (TIANJIN) CO LTD
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Problems solved by technology

However, there is currently no complete synthetic route report

Method used

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  • Synthetic method of 7-tert-butyl 3-ethyl 8-methyl-5,6 dihydrotriazolopyrazine 3,7(8H) phthalate ester
  • Synthetic method of 7-tert-butyl 3-ethyl 8-methyl-5,6 dihydrotriazolopyrazine 3,7(8H) phthalate ester
  • Synthetic method of 7-tert-butyl 3-ethyl 8-methyl-5,6 dihydrotriazolopyrazine 3,7(8H) phthalate ester

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Experimental program
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Embodiment

[0010] Synthesis of hydrazino-3-methylpyrazine

[0011]

[0012] Add 748 g of hydrazine hydrate to 300 g of compound 1 in ethanol at 20°C, and stir magnetically at 90°C for 12 hours after the addition. After the raw materials have been completely reacted, the reaction liquid is concentrated in vacuum, and the filter cake is beaten with about 1 L of dichloromethane to remove excess hydrazine hydrate. The filter cake was transferred to a one-necked bottle and dried under vacuum. 400 g of compound 2 was obtained as a yellow solid.

[0013] Synthesis of Ethyl-8-Methyl-[1,2,4]triazolo[4,3-a]pyrazine-3-carboxylate

[0014]

[0015] 435 g of Compound 2 was dissolved in 5 L of diethyl oxalate, and the reaction solution was magnetically stirred at 25°C for 5 hours. After the raw material is completely reflected, the oil pump spins the diethyl oxalate away, and the solid is beaten and filtered with about 2L of dichloromethane. The filter cake is a by-product and washed twice wi...

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Abstract

The invention relates to a preparation method of 7-tert-butyl 3-ethyl 8-methyl-5,6 dihydrotriazolopyrazine 3,7(8H) phthalate ester and mainly solves the technical problems that at present, a compoundis not suitable for an industrial preparation method. The preparation method comprises the following steps: taking 2-chloro-3-methylpyrazine as a starting raw material and preparing the 7-tert-butyl-3-ethyl-8-methyl-5,6-dihydro-[1,2,4]triazol[4,3-a]pyrazine-3,7(8H)-phthalate ester through three-step reaction. A reaction formula is shown in the Specification. The 7-tert-butyl-3-ethyl-8-methyl-5,6-dihydro-[1,2,4]triazol[4,3-a]pyrazine-3,7(8H)-phthalate ester obtained by the preparation method provided by the invention is a useful intermediate or a product for synthesis of multiple drugs.

Description

technical field [0001] The present invention relates to 7-tert-butyl-3-ethyl-8-methyl-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-3,7( 8H)-Synthetic method of dicarboxylate. Background technique [0002] 7-tert-butyl-3-ethyl-8-methyl-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-3,7(8H)- Diformyl esters (CAS: 1174644-71-3) and related derivatives have important applications in medicinal chemistry and organic synthesis and have excellent prospects. However, there is no complete synthetic route report so far. Therefore, it is of great significance to develop a synthetic method that is easy to obtain cheap raw materials, easy to operate, easy to control the reaction in batch production, and suitable for the overall yield. Contents of the invention [0003] The purpose of this invention is to develop a kind of raw material that has cheap, easy to operate, can enlarge, three steps higher yield 7-tert-butyl-3-ethyl-8-methyl-5,6-dihydro-[1, 2,4] Triazolo[4,3-a]pyrazine-3,7(8H)-di...

Claims

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Application Information

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IPC IPC(8): C07D487/04
Inventor 徐学芹周强安自强刘月领何燕平焦家盛王瑞琪吴艳徐富军于凌波马汝建
Owner WUXI APPTEC (TIANJIN) CO LTD
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