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Environment-friendly synthetic method for 2-amino-5,8-disubstituted-[1,2,4]triazole[1,5-c]pyrimidine

A synthetic method and a two-substitution technology, applied in the field of compound synthesis, can solve the problems of increased post-processing difficulty, easy decay and easy degradation, and high production cost, and achieve the effects of being beneficial to environmental protection, easy to control the reaction process, and mild reaction conditions.

Active Publication Date: 2014-04-23
JIANGSU FUDING CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, the existing methods all use highly toxic and dangerous substances (such as BrCN), whose activity is very unstable, easy to decay and degrade, highly toxic, difficult to purchase, easy to produce a large amount of highly polluted wastewater (such as cyanide-containing wastewater), and greatly increase post-treatment Difficulty, high production cost, low product yield (total yield less than 40%), etc.

Method used

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  • Environment-friendly synthetic method for 2-amino-5,8-disubstituted-[1,2,4]triazole[1,5-c]pyrimidine
  • Environment-friendly synthetic method for 2-amino-5,8-disubstituted-[1,2,4]triazole[1,5-c]pyrimidine
  • Environment-friendly synthetic method for 2-amino-5,8-disubstituted-[1,2,4]triazole[1,5-c]pyrimidine

Examples

Experimental program
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Effect test

Embodiment 1

[0022]

[0023] Put 60mL of ethyl acetate and 1.0g of potassium thiocyanate into a 100mL three-necked bottle, add 1.1g of ethyl chloroformate dropwise at 50°C-55°C, react at 55°C-60°C for 2 hours after the addition, and cool down to 20°C- 30°C, remove potassium chloride by filtration. Add 1.3 g of 2,5-dimethoxy-4-aminopyrimidine to the filtrate, react at 20°C-30°C for 5-8 hours, follow-up analysis by HPLC, after the reaction is completed, cool and crystallize to obtain yellow crystal 4 -[4-(2,5-dimethoxypyrimidinyl)]-3-ethyl thiourate, 2.3g, purity 99%, yield about 92%.

[0024] Add 1.5 g of ethyl 4-[4-(2,5-dimethoxypyrimidinyl)]-3-thiouric acid, 0.5 g of hydroxylamine hydrochloride, and 1,4-dioxane into a 100 mL three-necked flask 10 mL, then added 1.2 g of triethylamine, further added methanol solution containing 0.5 g of sodium methoxide, stirred and reacted at 20°C to 30°C for 10 to 12 hours, followed by HPLC, after the reaction was completed, filtered to obtain a whit...

Embodiment 2

[0028] Put 40mL of ethyl acetate and 0.95g of sodium thiocyanate into a 100mL three-necked bottle, add dropwise a mixture of 0.9g of methyl chloroformate and 10mL of ethyl acetate at 40°C to 45°C, and react at 40°C to 50°C after adding After 3 hours, cool down to 20°C to 30°C, and remove sodium chloride by filtration. Add 1.25 g of 2-methyl-5-methoxy-4-aminopyrimidine to the filtrate, react at 20°C to 30°C for 6 to 10 hours, perform HPLC follow-up analysis, and cool to 10°C to 15°C after the reaction is completed. ℃, crystallized to obtain light yellow crystal 4-[4-(2-methyl-5-methoxypyrimidinyl)]-3-ethyl thiourate, 2.3g, purity 99%, yield about 92% .

[0029] Add 1.45 g of 4-[4-(2-methyl-5-methoxypyrimidinyl)]-3-thiouric acid ethyl ester, 1.0 g of hydroxylamine sulfate, and 1,4-dioxo Hexacyclic 15mL, then add 1.5g of pyridine, react at 20℃~30℃ for 4h, then add 2.5g of ethanol solution containing 0.6g of sodium ethoxide, stir and react at 25℃~30℃ for 8~10h, follow by HPLC, ...

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Abstract

A disclosed environment-friendly synthetic method for 2-amino-5,8-disubstituted-[1,2,4]triazole[1,5-c]pyrimidine comprises performing thiocyanation reaction on a chloroformate and a thiocyanate to obtain a thiocyanatoformate of a formula III compound; performing condensation reaction on the thiocyanatoformate and a formula IV compound to obtain a formula V compound; and performing a ring-closure reaction on the formula V compound under the effect of a hydroxylamine salt and a sodium alkoxide to obtain a formula I compound. The method provided by the invention employing routine raw material, is low in production cost and suitable for industrialized production, is short in reaction route, mild in reaction conditions and easily-controllable in reaction process, and does not generate various high-pollution wastewater during synthesis and is in favor of environment protection. Additionally, the synthetic route is shown in the specification.

Description

technical field [0001] The invention belongs to the field of compound synthesis, and in particular relates to a synthesis method of 2-amino-5,8-disubstituted [1,2,4]triazol[1,5-c]pyrimidine. Background technique [0002] 2-Amino-5,8-disubstituted [1,2,4]triazol[1,5-c]pyrimidine is an important chemical intermediate, which is often used in the synthesis of pharmaceutical compounds, such as pentafluoro The 2-amino-5,8-dimethoxy[1,2,4]triazol[1,5-c]pyrimidine used in the synthesis of sulcolam, etc. [0003] From 3-amino-8-methoxy-5-methylthio[1,2,4]triazole[4,3-c in U.S. Patent No. 5,858,924 by treating with ethacrylate and sodium methoxide in methanol ]pyrimidine to prepare 2-amino-5,8-dimethoxy[1,2,4]triazol[1,5-c]pyrimidine. 3-Amino-8-methoxy-5-methylthio[1,2 ,4] Triazol[4,3-c]pyrimidine. [0004] It is described in CN1436190A that from 3-amino-8-methoxy [1,2,4] triazolo [4,3-c] pyrimidine substituted by 5-chloro or 5-methoxy group by in an alcohol solvent and methylate ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 刘东卫
Owner JIANGSU FUDING CHEM