Pyrazolo[1,5-a]pyrimidines. Identification of the Privileged Structure and Combinatorial Synthesis of 3-(Hetero)arylpyrazolo[1,5-a]pyrimidine-6-carboxamides

Brian T. Gregg,* Dmytro O. Tymoshenko, Dana A. Razzano, and Matthew R. Johnson
Albany Molecular Research, Inc., 21 Corporate Circle, Albany, New York, 12212
J. Comb. Chem., 2007, 9 (3), pp 507–512
DOI: 10.1021/cc0700039
Publication Date (Web): April 18, 2007
Copyright © 2007 American Chemical Society

Abstract

Abstract Image

The pyrazolo[1,5-a]pyrimidine class of compounds has been identified as a privileged structure for library synthesis on the basis of several key characteristics of the core molecule. A chemical set in excess of 400 compounds was synthesized to give 3,6,7-substituted pyrazolo[1,5-a]pyrimidinecarboxamides 9. To facilitate the rapid preparation of this library, a preparative strategy included the synthesis of activated p-nitrophenyl esters, followed by subsequent scavenging of the p-nitrophenol leaving group. Excess reagents were also removed using scavenging reagents that were found to be compatible with the synthetic methodology and that afforded target compounds in acceptable purity and yields.

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History

  • Published In Issue May 14, 2007
  • Received January 2, 2007

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