Sodium Carbonate → HCID 57829820, compound

Participants

Reaction Steps

Palladium(II) acetate (5.4 mg, 0.024 mmol) and 2-(dicyclohexylphosphino)biphenyl (17 mg, 0.048 mmol) were stirred in dioxane (2.7 mL) for 10 minutes at 20° C. under an atmosphere of nitrogen. Sodium tert.-butoxide (44 mg, 0.45 mmol), 3-methoxy-4-(4-methyl-imidazole-1-yl)-phenylamine (61 mg, 0.30 mmol) and (5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-(2-chloro-5-fluoro-pyrimidin-4-yl)-amine (94 mg, 0.33 mmol, WO2008099210) were added. The reaction was heated for 30 minutes to 200° C. in a microwave oven. Palladium(II) acetate (5.4 mg, 0.024 mmol), 2-(dicyclohexylphosphino)-biphenyl (17 mg, 0.048 mmol), sodium carbonate (48 mg, 0.45 mmol), (5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-(2-chloro-5-fluoro-pyrimidin-4-yl)-amine (85 mg, 0.3 mmol) and dioxane (1 mL) were added. The reaction was heated again for 30 minutes to 200° C. in a microwave oven. Water was added to the cooled reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using dichloromethane and then dichloromethane/methanol (19:1 v/v) as eluent to yield the title compound as a yellow solid (41 mg, 30%). MS ISP (m/e): 451.2 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.02 (s, 1H), 7.60 (s, 1H), 7.30 (s, 1H), 7.09 (d, 1H), 7.03 (m, 2H), 6.82 (s, 1H), 6.45 (br s, 1H, NH), 6.11 (s, 1H), 3.73 (s, 3H), 3.72 (s, 3H), 2.29 (s, 3H), 1.32 (s, 9H).

Provenance & Evidence