Imidazole → HCID 11441884, compound

Participants

Reaction Steps

Sodium hydride (60% in oil, 32 mg, 0.78 mmol) was added to a solution of [5-(4-fluoro-benzenesulfonyl)-2-methylpyrimidin-4-yl]-(2,4,6-trimethylphenyl)-amine (100 mg, 0.26 mmol) and imidazole (53 mg, 0.78 mmol) in 1,4-dioxane (4 mL). The mixture was stirred at room temperature for 10 min and then heated at reflux under N2 for 24 h. The mixture was cooled to room temperature, and saturated aqueous NH4Cl was added. The mixture was extracted three times with CH2Cl2, and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (EtOAc) to provide the target compound (56 mg, 50%) as a white solid: mp 230–232° C.; 1H NMR (500 MHz, DMSO-d6) δ 8.82 (s, 1H), 8.48 (br s, 1H), 8.44 (s, 1H), 8.34 (d, J=8.7 Hz, 2H), 7.95 (d, J=8.7 Hz, 2H), 7.90 (s, 1H), 7.15 (s, 1H), 6.89 (s, 2H), 2.25 (s, 3H), 2.24 (s, 3H), 1.86 (s, 6H); APCI MS m/z 434 [(M+H)+, calcd for C23H24N5O2S, 434.1].

Provenance & Evidence