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High-pressure synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4-d]pyrimidines

Authors
Journal
Bioorganic & Medicinal Chemistry Letters
0960-894X
Publisher
Elsevier
Publication Date
Volume
11
Issue
2
Identifiers
DOI: 10.1016/s0960-894x(00)00620-x

Abstract

Abstract The synthesis of enantiomerically pure C-6 substituted pyrazolo[3,4- d]pyrimidines has been performed by aromatic nucleophilic substitution of 4-amino-6-chloro-1-phenylpyrazolo[3,4- d]pyrimidine under conditions of high pressure at ambient temperature. Conventional synthetic conditions (reflux at atmospheric pressure) were unsuccessful. The S enantiomer 11 displayed higher affinity and selectivity for the adenosine A 1 receptor than the R enantiomer 12.

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