Water → HCID 21310545, compound

Participants

Reaction Steps

Added to a mixture of sodium hydride (0.05 g, 0.88 mmol) in DMSO (1 mL) was trimethyl sulfoxonium iodide (0.29 g, 1.3 mmol). After stirring the resultant mixture 1.5 h. (when gas evolution ceases), 1-(4-oxocyclohexyl)-4-(4-fluorophenyl)-5-[(2-methoxy)pyrimidin-4-yl]imidazole from example 1(j) (0.322 g, 0.88 mmol) suspended in dry THF (4 mL) was added and the mixture was stirred 4 h. The mixture was poured into H2O and extracted with EtOAc. The organic phase was dried (Na2SO4) and concentrated. The resulting residue was suspended in EtOAc/hexane (1:1) and filtered. The solid was purified by flash chromatography (silica gel 2% MeOH/CH2Cl2) to afford the title compound as white crystals (0.18 g, 53% yield) 1H NMR (CDCl3): δ 8.35 (d, 1H), 7.85 (s, 1H), 7.43 (q, 2H), 7.02 (t, 2H), 6.80 (d, 1H), 4.86 (m, 1H), 4.09 (s, 3H), 2.76 (s, 2H), 226 (m, 2H), 2.20-2.02 (m, 4H), 1.43 (d, 2H).

Provenance & Evidence