High-Pressure Synthesis of Enantiomerically Pure C-6 Substituted Pyrazolo[3,4-d]pyrimidines
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Poulsen, SA
Young, DJ
Quinn, RJ
Young, DJ
Quinn, RJ
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Prof D.L. Boger
Date
2001
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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 A1 receptor than the R enantiomer 12.
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Bioorganic & Medicinal Chemistry Letters
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11
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2
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Medicinal and biomolecular chemistry
Organic chemistry
Pharmacology and pharmaceutical sciences
History, heritage and archaeology