[H-].[Na+].Cl[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([S:10][CH3:11])[N:5]=1.[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16].[I-].C[N+]1C=CN(C)C=1>O1CCOCC1>[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([S:10][CH3:11])[N:5]=1)=[O:16]
Sodium hydride (60% dispersion in mineral oil, 598 mg, 14.94 mmol) was added to a stirring solution of 4-chloro-2-methylthiopyrimidine (1.45 mL, 12.45 mmol), 2-fluorobenzaldehyde (1.57 mL, 14.94 mmol) and 1,3-dimethylimidazolium iodide (517 mg, 4.15 mmol) (prepared as described in Org. Synth. (1986) 64:9) in 1,4-dioxane (20 mL). The resulting mixture was heated at reflux for 1 hour; it was then cooled and partitioned between EtOAc and water. The organic layer was separated and dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc, 95/5) to give 840 mg of (2-fluorophenyl)-(2-methylsulfanyl-pyrimidin-4-yl)-methanone.
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