5-Methylfurfural → 1,3-Dimethyl-10-(5-methylfuran-2-yl)-5-phenyl-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

6-(2-Hydroxyethyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (Int C) (244 mg, 0.815 mmol), bismuth triflate (50.9 mg, 0.082 mmol, 10 mol %) and EtOH (2.4 mL) were treated with 5-methylfuran-2-carbaldehyde (commercially available, 0.089 mL, 0.082 mmol). The mixture was heated to 100° C. for 10 min using microwave irradiation. A further portion of 5-methylfuran-2-carbaldehyde (25 μL) was added to the reaction mixture and heating continued at 100° C. for 5 min. A solid formed on cooling, which was collected by reduced pressure filtration and washed with EtOH followed by diethyl ether, affording the title compound.

Provenance & Evidence