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Method for synthesizing S-tert-butoxycarbonyl-4-6-dimethyl-2-mercaptopyrimidine

A technology of tert-butoxycarbonyl and mercaptopyrimidine is applied in the field of synthesis of S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine, which can solve the problems of inconvenient industrial production and achieve easy industrial production , Conditions are easy to control, the effect of low cost

Active Publication Date: 2014-07-23
SUZHOU HIGHFINE BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method requires two-step reactions, and requires the use of highly toxic reagents such as phosgene, making industrial production extremely inconvenient

Method used

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  • Method for synthesizing S-tert-butoxycarbonyl-4-6-dimethyl-2-mercaptopyrimidine
  • Method for synthesizing S-tert-butoxycarbonyl-4-6-dimethyl-2-mercaptopyrimidine
  • Method for synthesizing S-tert-butoxycarbonyl-4-6-dimethyl-2-mercaptopyrimidine

Examples

Experimental program
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Effect test

Embodiment 1

[0015] This example provides a synthesis method of S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine, which is implemented as follows:

[0016] 10 g of 4,6-dimethyl-2-mercaptopyrimidine at room temperature, (Boc) 2 O (Sinopharm Shanghai Chemical Reagent Company, chemically pure) 18g, triethylamine (Sinopharm Shanghai Chemical Reagent Company, chemically pure) 11g, DMAP (Sinopharm Shanghai Chemical Reagent Company, chemically pure) 0.87g added dichloromethane (Sinopharm Group Shanghai Chemical Reagent Company, chemically pure) in 90ml, slowly heated to 40°C, reacted for 5~7h, after the reaction, added dilute hydrochloric acid, adjusted the pH to 1-2, separated the organic layer, dried over sodium sulfate and then reduced pressure The solvent was evaporated, and ethyl acetate was added for recrystallization to obtain 14.4 g of the target compound with a yield of 84%. target compound 1 H NMR and mass spectral data are as follows:

[0017] 1 H NMR (CDCl 3 ,500MHz): δ=1....

Embodiment 2

[0020] This example provides a synthesis method of S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine, the specific implementation is as follows:

[0021] 10 g of 4,6-dimethyl-2-mercaptopyrimidine at room temperature, (Boc) 2 O (Sinopharm Shanghai Chemical Reagent Company, chemically pure) 17.3g, pyridine (Sinopharm Shanghai Chemical Reagent Company, chemically pure) 9.0g, DMAP (Sinopharm Shanghai Chemical Reagent Company, chemically pure) 0.87g was added to chloroform (Sinopharm Shanghai Chemical Reagent Company, Chemical Pure) into 90ml, slowly heated to 60°C, reacted for 3~5h, after the reaction, added dilute hydrochloric acid, adjusted the pH to 1-2, separated the organic layer, dried over sodium sulfate and evaporated under reduced pressure The solvent was removed, and acetonitrile was added for recrystallization to obtain 14.0 g of the target compound with a yield of 82%. target compound 1 H NMR and mass spectral data are as follows:

[0022] 1 H NMR (CDCl 3 ,5...

Embodiment 3

[0025] This example provides a synthesis method of S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine, the specific implementation is as follows:

[0026] 10 g of 4,6-dimethyl-2-mercaptopyrimidine at room temperature, (Boc) 2 O (Sinopharm Shanghai Chemical Reagent Company, chemically pure) 18.2g, N,N-Diisopropylethylamine (Sinopharm Shanghai Chemical Reagent Company, chemically pure) 14.7g, DMAP (Sinopharm Shanghai Chemical Reagent Company, chemically pure) ) 4.3g into acetonitrile (Sinopharm Shanghai Chemical Reagent Company, chemically pure) 80ml, slowly heated to 50°C, reacted for 3~5h, after the reaction, added dilute hydrochloric acid, adjusted the pH to 1-2, added dichloromethane The organic layer was separated by extraction, dried over sodium sulfate, and the solvent was distilled off under reduced pressure, and ethyl acetate was added for recrystallization to obtain 14.6 g of compound IV with a yield of 86%. target compound 1 H NMR and mass spectral data are as ...

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Abstract

The invention relates to a method for synthesizing S-tert-butoxycarbonyl-4-6-dimethyl-2-mercaptopyrimidine. 4-6-dimethyl-2-mercaptopyrimidine and di-tert-butyl dicarbonate are reacted in an organic solvent under the alkaline condition in the presence of a 4-dimethylamino-pyridine catalyst to form the S-tert-butoxycarbonyl-4-6-dimethyl-2-mercaptopyrimidine. The method is simple and short in synthetic route and high in yield; and moreover, expensive or highly toxic reagents are avoided, the condition is easy to control, the operation is convenient, the cost is low and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine. Background technique [0002] S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine (S-BOC-4,6-dimethyl-2-mercaptopyrimidine) is an acylating reagent used for BOC on amino groups Protective base. Currently, the synthesis literatures of S-BOC-4,6-dimethyl-2-mercaptopyrimidine are reported: US3932375, US3852290 and Bulletin of the Chemical Society of Japan, 1973, vol.46, p.1269-1270, etc. These reported synthetic methods all use 4,6-dimethyl-2-mercaptopyrimidine (compound 1) as a raw material, react with phosgene to obtain intermediate 2, and then react with tert-butanol to obtain the product. This method requires two-step reactions, and requires the use of highly toxic reagents such as phosgene, making industrial production extremely inconvenient. [0003] Contents of the invention ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/38
Inventor 朱勇叶智华刘新贵鲍彬史培忠
Owner SUZHOU HIGHFINE BIOTECH