Sodium Iodide → 3-ethyl-6-methyl-5-(2-methyl-2H-1,2,4-triazol-3-yl)-1H-pyridin-2-one

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Reaction Conditions

Reaction Steps

To a mixture of 3-ethyl-2-methoxy-6-methyl-5-(2-methyl-2H-1,2,4-triazol-3-yl)-pyridine (76 mg, 0.328 mmol) and sodium iodide (148 mg, 0.987 mmol) under a nitrogen atmosphere is added anhydrous acetonitrile (5 mL) followed by drop-wise addition of chlorotrimethylsilane (123 μL, 0.979 mmol). The reaction mixture is stirred at 60° C. under nitrogen for 12 hr. The reaction mixture is allowed to cool and then quenched with water (0.75 mL). After stirring for 30 min, the mixture is partitioned between water and dichloromethane. The dichloromethane layer is separated and the aqueous layer is extracted with ten further portions of dichloromethane. The combined organic layer is dried over magnesium sulfate and evaporated. The crude product is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (9:1). Fractions containing the product are combined and the solvent evaporated to give 3-ethyl-6-methyl-5-(2-methyl-2H-1,2,4-triazol-3-yl)-1H-pyridin-2-one (73 mg, 100% yield) as a cream solid. LC/MS: RT: 1.85 min, MS: m/e=219 (M+H); 1H NMR (400 MHz, d6-DMSO, δ, ppm): 11.92 (1H, s), 7.98 (1H, s), 3.74 (3H, s), 2.39 (2H, q), 1.09 (3H, t).

Provenance & Evidence