The chemistry of 4-azido-2-pyrimidinone nucleosides revisited

J Org Chem. 2005 Mar 4;70(5):1961-2. doi: 10.1021/jo0479765.

Abstract

Treatment of 4-azido-2-pyrimidinone nucleoside 1 with MeOH/K2CO3 or ammonium hydroxide led to derivatives 2 and 3, respectively. Both compounds derived from a nucleophilic addition at the modified base 2-position. These results contrast with the previously reported sensitivity of the 4-azido-2-pyrimidinone nucleoside 6-position to nucleophiles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides / chemistry*
  • Magnetic Resonance Spectroscopy / statistics & numerical data
  • Molecular Conformation
  • Nucleosides / chemical synthesis
  • Nucleosides / chemistry*
  • Pyrimidinones / chemistry*

Substances

  • Azides
  • Nucleosides
  • Pyrimidinones