Ammonia → 1-beta-d-Arabinofuranosyl-1H-imidazo[4,5-c]pyridin-4-amine

Participants

Reaction Steps

An improved process for producing a compound of the formula ##STR7## wherein X is NH2, OH or SH; R is hydrogen or acyl containing 2 or 3 carbon atoms; and R1 is hydrogen, acyl containing 2 or 3 carbon atoms or phosphate which comprises β-D-arabinofuranosylating 4-chloro-1H-imidazo-[4,5-c]pyridine with 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride; treating the resulting blocked nucleoside sequentially with hydrazine, Raney nickel and sodium in liquid ammonia to obtain 1-β-D-arabinofuranosyl-1H-imidazo[4,5-c]pyridin-4-amine and acylating, phosphorylating, treating with sodium nitrate then phosphorus pentasulfide to obtain the desired compounds wherein the improvement comprises treating 4-chloro-1H-imidazo[4,5-c]pyridine with sodium hydride in a suitable solvent to form the anion having the formula ##STR8## and β-D-arabinofuranosylating said anion with 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride.

Provenance & Evidence