Methyl iodide → 5-(3-bromo-phenyl)-3-methyl-2-methylsulfanyl-6-pyridin-4-yl-3H-pyrimidin-4-one

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Reaction Steps

To a 500 mL round bottom flask (RBF), was added ethyl (3-bromo-phenyl)acetate (10.3 g, 42.2 mmol), 4-cyanopyridine (4.4 g, 42.2 mmol) and 56 mL DMF. The mixture was stirred at room temperature under nitrogen. 42 mL 1 M KOtBu in tBuOH was added drop wise, and stirred for 1 h at rt. Methyl isothiocyanate (3.08 g, 42.2 mmol) was added in one portion, and stirred for another one hour at rt. The mixture was cooled down to 0° C., iodomethane (2.7 mL, 42.2 mmol) was added drop wise and stirred for 1 h at 0° C. To quench the reaction, 100 mL H2O was added. Yellow solid was precipitated. After filtration and washed with H2O, the 5-(3-bromo-phenyl)-3-methyl-2-methylsulfanyl-6-pyridin-4-yl-3H-pyrimidin-4-one was obtained in 9.2 g as pale yellow powder. MS (ES+): 388 (M+H)+; (ES−): 386 (M−H).

Provenance & Evidence