Potassium Carbonate → HCID 53251550, compound

Participants

Reaction Conditions

Reaction Steps

To N-[3-(2-bromo-1,3-thiazol-5-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (180 mg, 0.449 mmol) were added copper iodide (17.09 mg, 0.090 mmol), K2CO3 (124 mg, 0.897 mmol), 1,3-oxazolidin-2-one (78 mg, 0.897 mmol) and dioxane. N,N-dimethylethane-1,2-diamine (7.91 mg, 0.090 mmol) was added and the reaction was allowed to stir at 110° C. for 4 hours. The reaction mixture was diluted with ethyl acetate washed with brine, dried over Na2SO4 and concentrated in vacuo. The product was purified by column chromatography on silica gel (50-70% ethyl acetate/hexane) to afford 3-[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]-1,3-oxazolidin-2-one (98 mg, 54%) as an off-white solid. APCI [M+H]+ m/z 408.0. 1H NMR (500 MHz, CDCl3): δ 8.71 (d, J=4.9 Hz, 1H); 8.08 (s, 1H); 7.69 (s, 1H); 7.51 (d, J=8.1 Hz, 1H); 7.43-7.38 (m, 2H); 7.30 (s, 1H); 7.11 (d, J=4.9 Hz, 1H); 4.68 (t, J=8.1 Hz, 2H); 4.39 (t, J=8.1 Hz, 2H). rhSYK activity=+++.

Provenance & Evidence