Methyl iodide → 2-(Difluoro(5-fluoropyridin-2-yl)methyl)-7-methyl-4-(methylthio)quinazoline

Participants

Reaction Steps

To a solution of 2-(difluoro(5-fluoropyridin-2-yl)methyl)-7-methylquinazoline-4-thiol (243 mg, ˜0.75 mmol) in isopropanol (5 mL) was added 1N NaOH (1.13 mL, 1.13 mmol), and the mixture was stirred at rt for 5 min. Iodomethane (0.06 mL, 0.90 mmol) was then added and the mixture was stirred at room temperature for 5 min. The mixture was concentrated under reduced pressure to afford a yellow solid that was collected and washed with water and methanol to afford 2-(difluoro(5-fluoropyridin-2-yl)methyl)-7-methyl-4-(methylthio)quinazoline as a light yellow solid (152 mg, 60%). (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ 8.57-8.66 (m, 1H), 7.93-8.12 (m, 3H), 7.85 (s, 1H), 7.62-7.71 (m, 1H), 2.56 (s, 3H), 2.53 (s, 3H). LCMS (ESI) m/z 336 (M+H)+.

Provenance & Evidence