Ethanol → HCID 89579938, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-5-phenyl-thieno[2,3-d]pyrimidine (1.00 g, 4.05 mmol), nortropinone hydrochloride (0.983 g, 6.08 mmol) and triethylamine (1.71 mL, 12.2 mmol) in THF (20 mL) was heated to 70° C. overnight. Ethanol (20 mL) was added and the mixture was heated to 70° C. for 3 hr. Further batches of nortropinone hydrochloride (0.983 g, 6.08 mmol) and triethylamine (1.71 mL, 12.2 mmol) were added and the mixture was heated to 70° C. overnight. Further batches of nortropinone hydrochloride (0.983 g, 6.08 mmol) and triethylamine (1.71 mL, 12.2 mmol) were added and the mixture was heated to 70° C. over 3 nights. It was cooled to room temperature and diluted with dichloromethane (40 mL) and water (40 mL). The layers were separated and the aqueous was extracted with dichloromethane (2×40 mL). The combined organic layers were washed with brine (1×40 mL), filtered through a hydrophobic frit and evaporated to give a brown oil. Mass: 3.21 g. This was purified by silica chromatography (100 g cartridge; eluent petrol/ethyl acetate 0 to 40%). Fractions corresponding to the main peak were combined and evaporated to give 8-(5-phenylthieno[2,3-d]pyrimidin-4-yl)-8-azabicyclo[3.2.1]octan-3-one as a white solid (0.99 g).

Provenance & Evidence