Electrophilic and nucleophilic substitution reactions of 8-pyridyl- and 8-(1-methylpyridino)-purines

Journal of the Chemical Society C: Organic Pub Date: DOI: 10.1039/J39690001831

Abstract

When 6-methylthio-8-(3- or 4-pyridyl)purines are treated with methyl iodide in dimethylformamide, they are first quaternised at the pyridyl nitrogen. The quaternary 8-(1-methylpyridino)-substituent then prevents further alkylation in the purine ring, with the exception of position 3. In contrast, in the 8-(2-pyridyl) series, alkylation proceeds only at the purine nitrogens, the only exception being the 3-methyl-6-methylthio-derivative, which undergoes quaternisation.

In the isomeric 3-methyl-6-methylthio-8-pyridylpurines, the rates of quaternisation follow the order 4-pyridyl > 3-pyridyl > 2-pyridyl.

A quaternary 8-pyridyl substituent enhances thiohydrolysis of the 6-methylthio-group.

The synthesis and physical properties of 8-pyridylhypoxanthines, 6-mercapto-8-pyridylpurines, and their N- and S-methyl derivatives are described.

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