Synthetic Strategies to 9-Substituted 8-Oxoadenines

Abstract

Three synthetic routes to 9-substituted 8-oxoadenines have been studied: bromination of adenine followed by N-9-alkylation/arylation and finally hydrolysis; bromination of adenine, hydrolysis, and N-functionalization as the last step; and N-9-alkylation of adenine, halogenation, and finally hydrolysis. As long as the N-9-functional group is compatible with conditions required for introduction of the halogen, the latter strategy was the most efficient. Also, a strategy starting from 5-amino-4,6-dichloropyrimidine was found to be a very good alternative for synthesis of 9-substituted 8-oxoadenines.

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GRAPHICAL ABSTRACT

Keywords:

• Halogenation
• hydrolysis
• N-alkylation
• 8-oxoadenine

ACKNOWLEDGMENT

The Norwegian Research Council is gratefully acknowledged for partial financing of the Bruker Avance instruments used in this study.

Notes

^a Isolated yields

^b Taken from Ref. 17.