Synthesis and Biological activity of Some PyrroloPyrimidine Compounds.
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Date
2013
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Sebha University
Abstract
The present work was planned to synthesize some heterocyclic compounds containing pyrrolo[2,3-d]pyrimidines.
Our approach to the synthesis of the target compounds started through the hydrolysis of 6-ethylthio-4-methyl-2-(p-methoxyphenyl)pyrimidine-5-carbonitrile by refluxing in ethanol containing sodium hydroxide to give the corresponding sodium salt derivative which in turn was acidified to give 5-cyano-4-methyl-2-(p-methoxyphenyl)pyrimidin-6(H)one. Chlorination of the 5-Cyano-4-methyl-2-(р-methoxyphenyl)pyrimidin-6(1H)-one afforded 6-Chloro-4-methyl-2-(p-methoxyphenyl)pyrimidin-5-carbonitrile, which reacted with ethyl glycinate hydrochloride to give Ethyl (5-cyano-4-methyl-2-(p-methoxyphenyl)yrimidin-6-yloxy)acetate, which underwent cyclization to give the ethyl 5-amino-4-methyl-2-(p-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate. The reaction of 5-Cyano-6-chloro-4-methyl-2-(р-methoxyphenyl)pyrimidine with piperidine, and morpholine, gave the 4-Methyl-6-(morpholin-4-yl)-2-(р-methoxyphenyl)pyrimidine-carbonitrile and 4-Methyl-6-(morpholin-4-yl)-2-(р-methoxyphenyl)pyrimidine-5-carbonitrile respectively .
The Ethyl 5-amino-4-methyl-2-(р-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate was used as key intermediates in the synthesis of other pyrrolo[2,3-d]pyrimidine derivatives, pyrimido[4\,5\:4,5]pyrrolo[2,3-d]pyrimidines and triazolopyrro lopyrimidines by reaction with different reagents .
Seven compounds were selected and screened in vitro for their antimicrobial activity against four strains of bacteria and two fungal species .
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Keywords
pyrrolopyrimidines, Pyrimidopyrimidines, synthesis , Biological activity