Diethyl Ether → 3-(10-(5-Chlorofuran-2-yl)-1,3-dimethyl-2,4-dioxo-2,3,4,7,8,10-hexahydro-1H-pyrimido[4',5':3,4]pyrrolo[2,1-c][1,4]thiazin-5-yl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

A suspension comprising 3-(6-(2-mercaptoethyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile (Intermediate G) (150 mg, 0.441 mmol), 5-chlorofuran-2-carbaldehyde (57.5 mg, 0.441 mmol) and bismuth triflate (28.9 mg, 0.044 mmol) in toluene (5 ml) was heated to 100° C. for 10 min using microwave radiation. After cooling to RT, the reaction mixture was diluted with EtOAc (25 ml) and washed with water. The layers were separated and the aqueous extracted with EtOAc (3×20 ml). The combined organics were dried over MgSO4, filtered and concentrated to yield a brown oil. Purification was carried out by chromatography on silica eluting with 0-45% EtOAc in iso-hexane. The relevant fraction were combined and concentrated in vacuo to yield a pale yellow oil. Diethyl ether (5 ml) was added to the oil to give a white solid. The solid was isolated by suction filtration to afford the title compound.

Provenance & Evidence