Utilization of tetrabutylammonium triphenyldifluorosilicate (TBAT) in the synthesis of 6-fluoropurine nucleosides

Nucleosides Nucleotides. 1999 Oct;18(10):2327-33. doi: 10.1080/07328319908044885.

Abstract

Tetrabutylammonium triphenydifluorosilicate (TBAT) has been found to be a useful reagent for the conversion of 6-chloropurine nucleosides to 6-fluoropurine derivatives. The 6-chloropurine nucleosides were reacted with trimethylamine to form quaternary trimethylammonium salts which were treated in situ with TBAT in DMF to effect conversion to the 6-fluoro derivatives in yields of 59-72%.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Nucleosides / chemical synthesis*
  • Organosilicon Compounds / chemistry*
  • Purines / chemical synthesis*
  • Purines / chemistry*
  • Quaternary Ammonium Compounds / chemistry*

Substances

  • Nucleosides
  • Organosilicon Compounds
  • Purines
  • Quaternary Ammonium Compounds
  • tetrabutylammonium triphenyldifluorosilicate
  • 6-fluoropurine
  • 6-chloropurine