Potassium Iodide → 6-(tert-Butyl)-3-methylselenopheno[3,2-d]1,2,3-triazin-4-one

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Reaction Steps

To a solution of 6-(tert-butyl)-3H-selenopheno[3,2-d]1,2,3-triazin-4-one (2.0 g, 7.78 mmol) in acetone (70 mL) was added sequentially potassium carbonate (2.14 g, 15.56 mmol), iodomethane (0.58 mL, 9.3 mmol) and potassium iodide (catalytic) at rt and the mixture was stirred at rt for 16 h. The solution was filtered and the solids were washed with acetone. Acetone was evaporated under reduced pressure and the residue was chromatographed over silica gel column using chloroform-methanol (95:05) as eluents to give the product as a off-white color solid (1.0 g, 47%), which was recrystallized from chloroform-methanol (700 mg, 34%), mp 98-100° C. IR (neat) νmax 2961, 1679, 1242, 1220, 1001, 969 cm−1; 1H NMR (400 MHz, CDCl3): δ 7.58 (1H, s, H-7), 4.04 (3H, s, —NCH3), 1.48 (9H, s, tert-butyl); 13C NMR (100 MHz, CDCl3): δ 176.0, 157.5, 154.7, 128.8, 121.5, 37.5, 37.3, 32.5; LC-MS (positive ion mode): m/z 292, 294 (M+Na)+.

Provenance & Evidence