Selective metalation of 6-methylpurines: synthesis of 6-fluoromethylpurines and related nucleosides.
A selective metalation at the 6-CH3 over C-8 of 6-methylpurine derivative 6 was observed with softer counter cation (Na+ or K+) of the base, while the harder Li+ showed no selectivity. In the presence of N-fluorobenzenesulfonamide (NFSI), this property was utilized for the synthesis of 6-fluoromethylpurine derivatives 4 and 5 as potential toxins for suicide gene therapy.
Hassan
Abdalla E A
AE
Drug Discovery Division, Southern Research Institute, Birmingham, Alabama, USA. ahassan@services.pharmasset.com
Parker
William B
WB
Allan
Paula W
PW
Montgomery
John A
JA
Secrist
John A
JA
D015316:Genetic Therapy / Q000379:methods; D007202:Indicators and Reagents; D008670:Metals; D008745:Methylation; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D011687:Purines / Q000138:chemical synthesis / Q000737:chemistry*
D007202:Indicators and Reagents; D008670:Metals; D011684:Purine Nucleosides; D011687:Purines; C035106:6-fluoropurine