Utilization of tetrabutylammonium triphenyldifluorosilicate (TBAT) in the synthesis of 6-fluoropurine nucleosides.
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%.
Gurvich
V
V
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA.
Kim
H Y
HY
Hodge
R P
RP
Harris
C M
CM
Harris
T M
TM
D009705:Nucleosides / Q000138:chemical synthesis*; D017646:Organosilicon Compounds / Q000737:chemistry*; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
D009705:Nucleosides; D017646:Organosilicon Compounds; D011687:Purines; D000644:Quaternary Ammonium Compounds; C403764:tetrabutylammonium triphenyldifluorosilicate; C035106:6-fluoropurine; C079308:6-chloropurine