Selective metalation of 6-methylpurines: synthesis of 6-fluoromethylpurines and related nucleosides.

Selective metalation of 6-methylpurines: synthesis of 6-fluoromethylpurines and related nucleosides.

Nucleosides, nucleotides & nucleic acids (2003-10-21)

Abdalla E A Hassan, William B Parker, Paula W Allan, John A Montgomery, John A Secrist

摘要

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.

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