Phenethylamine → 6-[(2,2-Diphenylethyl)amino]-9-[(2R,3R,4S,5R)-5-(2-ethyl-2H-tetrazol-5-yl)-3,4-dihydroxytetrahydro-2-furanyl]-N-(2-phenylethyl)-9H-purine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 9-[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate (Preparation 30) (100 mg, 0.15 mmol) and 2-phenylethylamine (0.2 ml, 1.58 mmol) were heated together under a nitrogen atmosphere at 130° C. for three hours. The mixture was allowed to cool to room temperature and was then purified by column chromatography on silica gel eluting with a gradient system of ethyl acetate gradually changing to ethyl acetate:methanol (95:5 by volume). Product containing fractions were evaporated and the resulting solid was triturated with ether, filtered and dried to afford the title compound as a white powder (50 mg).

Provenance & Evidence