A FACILE SYNTHESIS OF NEW 4-(PHENYLAMINO)THIENO[3,2-d]PYRIMIDINES USING 3-AMINOTHIOPHENE-2-CARBOXAMIDE

doi:10.1515/HC.2007.13.1.33

Paper

A FACILE SYNTHESIS OF NEW 4-(PHENYLAMINO)THIENO[3,2-d]PYRIMIDINES USING 3-AMINOTHIOPHENE-2-CARBOXAMIDE

Published 2007 · Yang-Heon Song

Heterocyclic Communications

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10

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Abstract

Several new 4-(phenylamino)thieno[3,2-</]pyrimidine derivatives 3 were synthesized in high yield by the reaction of aniline derivatives and 4-chlorothieno[3,2-i/]pyrimidine that can be easily prepared using 3-aminothiophene-2-carboxamide. Introduction Thienopyrimidine derivatives have been found to have good medicinal and biological activities. Recently, a novel class of thieno[3,2-t/|pyrimidine 1 has been identified as potent inhibitors of VEGF receptor-2 kinase, which is a key component of the signaling pathway responsible for the sprouting and maturation of new blood vessels from tumors. New thieno[2,3-c/]pyrimidine derivatives 2 were also prepared and investigated as selective and potent ligands for the 5-HT3 receptor. 5-HT3 receptor ligands have potential therapeutic applications in the treatment of psychosis, memory impairment, and drugs abuse. Since a variety of thienopyrimidine derivatives are needed for their biological importance, we herein wish to report a facile method for the preparation of new 4-(phenylamino)thieno[3,2-i/jpyrimidine derivatives 3 using 3-aminothiophene-2-carboxamide 4 in stead of methyl 3-aminothiophene-2carboxylate. Results and Discussion The cyclization reaction of methyl 3-aminothiophene-2-carboxylate with formic amide was not efficient in forming 5 by previous known method. Yield of the product does not exceed 50% and the reaction needs two steps, a very high temperature and longer reaction time. We found a facile synthetic route to 3 started from the condensation reaction of 3-aminothiophene-2-carboxamide 4 s with excess 2 3

Study Snapshot

This study presents a facile method for synthesizing new 4-(phenylamino)thieno[3,2-i/j]pyrimidine derivatives using 3-aminothiophene-2-carboxamide, offering potential therapeutic applications in psychosis, memory impairment, and drug abuse.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

A FACILE SYNTHESIS OF NEW 4-(PHENYLAMINO)THIENO[3,2-d]PYRIMIDINES USING 3-AMINOTHIOPHENE-2-CARBOXAMIDE

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