Phenoxide leaving group SNAr strategy for the facile preparation of 7-amino-3-aryl pyrazolo[1,5-a]pyrimidines from a 3-bromo-7-phenoxypyrazolo[1,5-a]pyrimidine intermediate

John G. Catalano, Vishwanath Gaitonde, Mallesh Beesu, Anna L. Leivers, J. Brad Shotwell

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

We have discovered a 3-bromo-7-phenoxypyrazolo[1,5-a]pyrimidine intermediate that allows for the direct sequential funtionalization of the 3-position and 7-position of a pyrazolo[1,5-a]pyrimidine scaffold. The intermediate and general method described herein offer an improvement over prior methods, particularly in cases where multiple unique 3-aryl substituents are to be incorporated in conjunction with multiple unique 7-amino substituents.

Original languageEnglish (US)
Pages (from-to)6077-6079
Number of pages3
JournalTetrahedron Letters
Volume56
Issue number44
DOIs
StatePublished - Oct 28 2015

Bibliographical note

Funding Information:
The authors wish to acknowledge the members of the Antiviral Discovery Performance Unit, as well as the Analytical and Separations groups at GlaxoSmithKline for their support and camaraderie. This work was financially supported by GlaxoSmithKline.

Publisher Copyright:
© 2015 Elsevier Ltd. All rights reserved.

Keywords

  • Heterocycle
  • Phenoxide
  • Pyrazolo[1,5-a]pyrimidine
  • SNAr
  • Suzuki

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