Sodium Iodide → HCID 178435580, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-ethyl-2-methoxy-6-methyl-5-(5-methyl-1H-1,2,4-triazol-3-yl)pyridine (90 mg, 0.413 mmol) and sodium iodide (194 mg, 1.29 mmol) under a nitrogen atmosphere is added anhydrous acetonitrile (5 mL) followed by drop-wise addition of chlorotrimethylsilane (162 μL, 1.29 mmol). The reaction mixture is stirred at 60° C. under nitrogen for 12 hr. LC/MS shows the reaction is incomplete. Further chlorotrimethylsilane (100 μL) is added and heating continued for 6 hr. The reaction mixture is allowed to cool and then quenched with water (0.7 mL). After stirring for 30 min the reaction mixture is evaporated to dryness. The residue is purified by flash chromatography on a 5-gram silica gel cartridge by elution with 2-propanol. Fractions containing the product are combined, evaporated, triturated with acetonitrile and re-purified by flash chromatography on a 5-gram silica gel cartridge by elution with 2-propanol. Fractions containing the product are combined and the solvent evaporated. The resulting residue is triturated with acetonitrile to give 3-ethyl-6-methyl-5-(5-methyl-2H-1,2,4-triazol-3-yl)-1H-pyridin-2-one (47 mg, 50% yield) as a cream solid. LC/MS: RT: 1.77 min, MS: m/e=219 (M+H); 1H NMR (δ, ppm): 13.99 (1H, s), 11.59 (1, br.s), 7.78 (1H, s), 2.41 (2H, q), 2.37 (3H, s), 1.10 (3H, t).

Provenance & Evidence