Facile synthesis of 8-azido-6-benzylaminopurine

Nucleosides Nucleotides Nucleic Acids. 2011 Jul-Aug;30(7-8):503-11. doi: 10.1080/15257770.2011.602655.

Abstract

Bromination of 6-benzylaminopurine (1) with Br(2) in AcOH in the presence of AcONa afforded 6-benzylamino-8-bromopurine (2) in 59% yield. The position of bromination was confirmed by direct transformation of bromide 2 by reaction with NaN(3) in dimethyl sulfoxide to 8-azido-6-benzylaminopurine (3) in a yield of 70% and comparison of its properties with the known compound 2-azido-6-benzylaminopurine (11). Compounds 3 and 11 were checked for their biological activity in specific biotests based on the primary cytokinin effects in living plants. Both synthesized compounds displayed effects similar to the typical cytokinin 6-benzylaminopurine (1).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides / chemical synthesis*
  • Azides / chemistry
  • Benzyl Compounds / chemical synthesis*
  • Benzyl Compounds / chemistry
  • Chemistry Techniques, Synthetic / economics
  • Chemistry Techniques, Synthetic / methods*
  • Cytokinins / chemical synthesis*
  • Cytokinins / chemistry
  • Halogenation
  • Plants / chemistry*
  • Purines / chemical synthesis*
  • Purines / chemistry

Substances

  • Azides
  • Benzyl Compounds
  • Cytokinins
  • Purines
  • benzylaminopurine