5-Chloro-2-furaldehyde → (8R)-10-(5-chlorofuran-2-yl)-5-(3-fluorophenyl)-8-(hydroxymethyl)-1,3-dimethyl-7,8-dihydro-1H-pyrimido[4',5':3,4]pyrrolo[2,1-c][1,4]oxazine-2,4(3H,10H)-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-6-(2,3-dihydroxypropyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (step 2) (806 mg, 2.320 mmol), bismuth triflate (305 mg, 0.464 mmol) and 5-chlorofuran-2-carbaldehyde (commercial) (333 mg, 2.55 mmol) in ethanol (13.6 mL) was heated under microwave irradiation at 100° C. for 25 mins. The mixture was evaporated under vacuum. The residue was partitioned between 0.1 M HCl (50 mL) and DCM (100 mL) and extracted with DCM (3×100 mL). The combined organic extracts were dried over magnesium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-60% EtOAc/hexane afforded the title compound as a mixture of diastereomers.

Provenance & Evidence