Utilization Of Tetrabutylammonium Triphenyldifluorosilicate (TBAT) In The Synthesis of 6-Fluoropurine Nucleosides

Vadim Gurvich Department of Chemistry and Center in Molecular Toxicology, Vanderbilt University, Nashville, Tennessee, 37235

Hye-Young Kim Department of Chemistry and Center in Molecular Toxicology, Vanderbilt University, Nashville, Tennessee, 37235

Richard P. Hodge Department of Chemistry and Center in Molecular Toxicology, Vanderbilt University, Nashville, Tennessee, 37235

Constance M. Harris Department of Chemistry and Center in Molecular Toxicology, Vanderbilt University, Nashville, Tennessee, 37235

Thomas M. Harris Department of Chemistry and Center in Molecular Toxicology, Vanderbilt University, Nashville, Tennessee, 37235

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%.

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Utilization Of Tetrabutylammonium Triphenyldifluorosilicate (TBAT) In The Synthesis of 6-Fluoropurine Nucleosides

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Utilization Of Tetrabutylammonium Triphenyldifluorosilicate (TBAT) In The Synthesis of 6-Fluoropurine Nucleosides

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