1,1-Dichloroethane → HCID 66899098, compound

Participants

Reaction Steps

A mixture of 230 mg of 1-[2-(4-chloro-2,5-difluorophenyl)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperidin-4-one, 140 mg of ethyl 4-aminobutyrate hydrochloride, 0.1 ml of acetic acid, 5 ml of dichloroethane, and 5 ml of DMF was stirred at ambient temperature for 1 hour, here was then added 353 mg of sodium triacetoxyborohydride, and the mixture was stirred at ambient temperature for 19 hours. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture, the mixture was extracted twice with chloroform, the organic phase was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue obtained was purified by silica-gel column chromatography (chloroform-MeOH) to yield 128 mg of ethyl 4-({1-[2-(4-chloro-2,5-difluorophenyl)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperidin-4-yl}amino)butanoate and 91 mg of 1-{1-[2-(4-chloro-2,5-difluorophenyl)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperidin-4-yl}pyrrolidin-2-one. Recrystallization of the latter from EtOH gave 65 mg of 1-{1-[2-(4-chloro-2,5-difluorophenyl)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperidin-4-yl}pyrrolidin-2-one as colorless solid.

Provenance & Evidence