Reaction Steps
A mixture of sodium tert-butoxide (31 mg, 0.32 mmol), palladium acetate (3 mg, 0.013 mmol), and (S)-BINAP (11 mg, 0.018 mmol) in toluene (2 mL) was stirred at room temperature for 0.5 h. A warm suspension of 2-amino-4-(imidazo[1,2-a]pyridin-3-yl)pyrimidine (58 mg, 0.27 mmol) in toluene (4 mL) and 4-bromo-4′-morpholinobenzophenone (79 mg, 0.23 mmol) was added, and the mixture was heated at 100° C. for 4 h. The solvent was removed in vacuo, and the residue was partitioned between dichloromethane and water. The phases were separated and the organic layer was washed with brine, dried (MgSO4) and the solvent was removed in vacuo. The crude product was purified by column chromatography on silica gel using chloroform/ethanol, 98:2, as the eluent affording 25 mg (23% yield) of the title compound as a yellow solid: mp (decomp.) >237° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.18 (d, J=6.8 Hz, 1 H), 10.1 (s, 1 H), 8.68 (s, 1 H), 8.53 (d, J=5.4 Hz, 1 H), 7.96 (d, J=8.5 Hz, 2 H), 7.80 (d, J=8.9 Hz, 1 H), 7.73 (d, J=8.6 Hz, 2 H), 7.69 (d, J=8.7 Hz, 2 H), 7.56-7.51 (m, 2 H), 7.19 (t, J=6.8 Hz, 1 H), 7.05 (d, J=8.7 Hz, 2 H), 3.76 (s, 4 H), 3.33 (s, 4 H); 13C NMR (400 MHz, DMSO-d6) δ 193.0, 159.4, 157.6, 157.3, 153.9, 148.3, 144.3, 139.3, 131.9, 131.1, 131.0, 129.7, 127.5, 127.4, 121.3, 118.2, 117.7, 114.2, 113.3, 108.4, 66.2, 47.2; MS (TSP) 7 m/z 477 (M+1).
