Potassium Carbonate → HCID 71075371, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-5-fluoro-4-(tetrahydrofuran-3-yloxy)pyrimidine (70 mg, 0.32 mol), 4-[5-(3-amino-5-methylphenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one (Intermediate XX, 97 mg, 0.32 mmol), Pd2(dba)3 (29 mg, 0.032 mmol), XPhos (76 mg, 0.16 mmol) and potassium carbonate (89 mg, 0.64 mmol) were added to a flask. The flask was purged and flushed with argon (3×). Degassed tert-amyl alcohol (1.1 ml) was added, the reaction mixture was purged with nitrogen for 5 min, and then heated to 90° C. overnight. The mixture was cooled to room temperature, diluted with ethyl acetate, treated with water, and extracted with ethyl acetate (×3). The combined organics were washed with brine, dried over sodium sulfate, concentrated, and purified by Combiflash (methanol/dichloromethane eluant) to provide 109 mg (0.23 mmol, 70% yield) of 4-[5-(3-{[5-fluoro-4-(tetrahydrofuran-3-yloxy)pyrimidin-2-yl]amino}-5-methylphenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one. MS APCI: [M+H]+ m/z 485.1. 1H NMR (500 MHz, DMSO-d6) δ 9.53 (s, 1H), 8.30 (d, J=2.9 Hz, 1H), 7.59 (t, J=4.8 Hz, 1H), 7.57 (s, 1H), 7.48 (s, 1H), 7.34 (s, 1H), 6.95 (s, 1H), 5.64 (t, J=4.9 Hz, 1H), 4.16 (s, 2H), 3.97-3.73 (m, 6H), 3.21 (m, 2H), 2.32 (m, 1H), 2.26 (s, 3H), 2.10 (m, 1H), 1.77 (s, 2H). rhSyk=++

Provenance & Evidence