Water → HCID 25264241, compound

Participants

Reaction Steps

A solution of potassium permanganate (3.38 g, 17.0 mmol) in water (95 mL) was added to a solution of 2-methyl-5-[4-methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl]pyrazine (1.853 g, 11.52 mmol) in glacial acetic acid (45 mL). The resulting mixture was stirred at room temperature overnight. Solid sodium hydrogen sulfate was added in portions until the dark color disappeared giving a clear colorless solution. The product was partitioned between chloroform (350 mL) and water (50 mL), and the aqueous layer was extracted with chloroform (3×150 mL). The combined organic layer was neutralized with aq. NaOH (40 is mL, 6M) and saturated sodium bicarbonate (250 mL) until gas evolution ceased and pH ˜7. The organic layer was washed with brine (100 mL) and dried over sodium sulfate. Removal of the solvent in vacuo yielded the title compound (2.715 g, 93%, white solid). 1H NMR (300 MHz): 9.44 (s, 1H), 8.55 (s, 1H), 4.36 (s, 3H), 3.62 (s, 3H), 2.69 (s, 3H).

Provenance & Evidence