反应详情

温度

60 °C

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).

1. temperatureheating
2. waitcontinued for 6 hr
3. temperatureto cool
4. customquenched with water (0.7 mL)
5. stirringAfter stirring for 30 min the reaction mixture
6. customis evaporated to dryness
7. customThe residue is purified by flash chromatography on a 5-gram silica gel cartridge by elution with 2-propanol
8. additionFractions containing the product
9. customevaporated
10. customtriturated with acetonitrile
11. customre-purified by flash chromatography on a 5-gram silica gel cartridge by elution with 2-propanol
12. additionFractions containing the product
13. customthe solvent evaporated
14. customThe resulting residue is triturated with acetonitrile