Potassium Carbonate → N-(3-(5-Chloro-2-((3-Hydroxy-4-Morpholinophenyl)Amino)Pyrimidin-4-Yl)Phenyl)Acrylamide

Participants

Reaction Conditions

Reaction Steps

N-(3-(2,5-dichloropyrimidin-4-yl)phenyl)acrylamide (151 mg, 0.515 mmol), 5-amino-2-morpholinophenol (100 mg, 0.515 mmol) and potassium carbonate (178 mg, 1.287 mmol) were dissolved in t-BuOH (5 mL) and Pd2dba3 (9.43 mg, 10.30 μmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (11.92 mg, 0.021 mmol) were added and then the reaction mixture was heated via microwave irradiation to 140° C. for 1 h. Reaction was monitored by TLC. After completion of the reaction, it was allowed to cool to about room temperature, and then reaction mixture was extracted with ethyl acetate (2×50 mL). The organic phase was concentrated and the residue was purified by flash column chromatography (4% MeOH/DCM) to provide the title compound (120 mg, 50.0% yield) as an off white solid. 1HNMR (400 MHz, CD3OD): δ 8.43 (s, 1H), 8.36 (s, 1H), 7.68 (m, 2H), 7.53 (d, 1H, J=2.0 Hz), 7.46 (t, 1H, J=8.4 Hz), 7.02 (dd, 1H, J=2.4 & 8.8 Hz), 6.97 (d, 1H, J=8.4 Hz), 6.50-6.38 (m, 2H), 5.80 (dd, 1H, J=2.4 & 9.6 Hz), 3.83 (m, 4H), 2.93 (m, 4H). Mass: 452.1 [M+H]+.

Provenance & Evidence