Sodium cyanoborohydride → HCID 178457325, compound

Participants

Reaction Steps

A methanolic solution of 2-(1-amino-1-methylethyl)-N-(4-fluorobenzyl)-5,6-dihydroxypyrimidine-4-carboxamide (prepared as described in WO2003035076 A1) was treated with 3-(benzyloxy)propanal (1.5 eq.) and sodium cyanoborohydride (1.5 eq.). The mixture was stirred at room temperature overnight, solution was applied on a cation exchange resin. The resin was washed with methanol and desired product was eluted with 2 N ammonia solution in methanol. Evaporation of appropriate fractions followed by trituration with Et2O gave intermediate 2-(1-{[3-(benzyloxy)propyl]amino}-1-methylethyl)-N-(4-fluorobenzyl)-5,6-dihydroxypyrimidine-4-carboxamide. MS (ES) C25H29FN4O4 requires 468. Found: 469 (M+H+). The crude organic product was taken in methanol, treated with 1 eq. of 6N HCl and stirred under hydrogen atmosphere in the presence of catalytic amount of 10% palladium on charcoal. After overnight stirring, mixture was filtered through celite, filtrate was concentrated under reduced pressure and purified by cation exchange resin. The resin was washed with methanol and desired product was eluted with 2 N ammonia solution in methanol. Evaporation of appropriate fractions followed by trituration with Et2O gave title compound as a pink solid. MS (ES) C18H23FN4O4 requires 378. Found: 379 (M+H+).

Provenance & Evidence