Sulfuric Acid → 2-(Difluoro(5-fluoropyridin-2-yl)methyl)-4-(methylthio)quinazoline-8-carboxamide

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Reaction Conditions

Reaction Steps

To 2-(difluoro(5-fluoropyridin-2-yl)methyl)-4-(methylthio)quinazoline-8-carbonitrile from Example 35 step C (200 mg, 0.57 mmol) were added concentrated sulfuric acid (2.88 mL) and water (0.32 mL). The mixture was stirred at 65° C. for 1 h and then allowed to cool to rt. The mixture was neutralized by slow addition of saturated aq sodium bicarbonate and then extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to afford 2-(difluoro(5-fluoropyridin-2-yl)methyl)-4-(methylthio)quinazoline-8-carboxamide (191 mg, 92%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.60 (s, 3H) 7.89-8.15 (m, 4H) 8.36-8.44 (m, 1H) 8.62-8.69 (m, 1H) 8.71-8.79 (m, 1H) 9.28-9.39 (m, 1H).

Provenance & Evidence