Hydrochloric Acid → 6-((1-(4-chlorophenyl)cyclopentyl)methyl)-9-hydroxy-2-(1-phenylethyl)-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 9-(benzyloxy)-6-((1-(4-chlorophenyl)cyclopentyl)methyl)-2-(1-phenylethyl)-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione (37) (76 mg, 134 μmol, Eq: 1.00) in methanol (5 ml) was added HCl (conc) (195 mg, 163 μl, 5.35 mmol, Eq: 40) and the reaction mixture was heated at 70° C. for 48 hrs. The reaction mixture was neutralized with saturated aqueous NaHCO3 solution, extracted with dichloromethane, dried (MgSO4), concentrated, and chromatographed (silica gel, gradient 0 to 5% methanol-dichloromethane) to obtain an off-white solid. The solid was triturated with diethyl ether, filtered, and dried to obtain 6-((1-(4-chlorophenyl)cyclopentyl)methyl)-9-hydroxy-2-(1-phenylethyl)-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione (38) (off-white powder, 51 mg, 107 μmol, 79.8% yield).

Provenance & Evidence