Ammonia → 5,6-Diphenylfuro[2,3-d]pyrimidin-4-amine

Participants

Reaction Steps

56.9 mg (0.185 mmol) of 4-chloro-5,6-diphenylfuro[2,3-d]pyrimidine 51 and 0.930 mL (1.85 mmol) of 2.0 M ammonia in methanol were combined in a disposable sealed tube and stirred at RT for 15 minutes. The reaction was then heated at 70° C. for 1.5 h. At this point, an additional 0.930 mL (1.85 mmol) of 2.0 M ammonia in methanol was added and the resulting mixture was heated at 70° C. for 3 days, cooled to RT and concentrated. Flash chromatography (SiO2, gradient eluent: 2:1 hexanes-ethylacetate, 2:1 ethyl acetate-hexanes, 9:1 CH2Cl2-MeOH), afforded the title compound 4-methoxy-5,6-diphenylfuro[2,3-d]pyrimidine 53 and 5,6-diphenylfuro[2,3-d]pyrimidin-4-amine 52. Mass found: 303.0 (M+H+); Calculated for C19H14N2O2: 302.

Provenance & Evidence