Reversible carboxamide-mediated internal activation at C(6) of 2-chloro-4-anilino-1H-pyrrolo[2,3-d]pyrimidines

J Org Chem. 2008 Dec 5;73(23):9511-4. doi: 10.1021/jo8020693.

Abstract

A synthetic route to bisanilino-1H-pyrrolo[2,3-d]pyrimidines has been discovered, wherein the C(6)-chloride reactivity is necessarily enhanced via reversible acid-catalyzed internal activation of the pyrimidine ring by a C(1')-carboxamide moiety. Subsequent selective nucleophilic displacements at C(6) and C(1') constitute a one-pot tandem protocol for the rapid assembly of bisanilino-1H-pyrrolo[2,3-d]pyrimidines.

MeSH terms

  • Amides / chemistry*
  • Carbon / chemistry
  • Catalysis
  • Chemistry, Organic / methods*
  • Chlorides / chemistry
  • Drug Design
  • Models, Chemical
  • Pyrimidines / chemistry*
  • Pyrroles / chemistry*

Substances

  • 4,6-bis-anilino-1H-pyrrolo(2,3-d)pyrimidine
  • Amides
  • Chlorides
  • Pyrimidines
  • Pyrroles
  • Carbon