Ethanol → [1,2,4]Triazolo[1,5-a]pyrazin-2-amine

Temperature

65 °C

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 270a (6.00 g, 26.43 mmol, 1.0 eq.), hydroxylamine hydrochloride (3.32 g, 47.52 mmol, 1.8 eq.), DIPEA (12 mL), ethanol (40 mL), and methanol (40 mL). The reaction mixture was stirred at 65° C. for 16 hours. After the reaction was complete, it was cooled to room temperature and concentrated to a volume of around 20 mL under reduced pressure. The resulting suspension was collected by filtration and the solid was washed with 60:1 dichloromethane/ethanol (50 mL) to afford 270b (3.3 g, 92%) as a white solid. MS-ESI: [M+H]+ 136.3. 1H NMR (500 MHz, DMSO-d6) δ 8.84 (d, J=1.0 Hz, 1H), 8.70 (dd, J=1.0, 4.0 Hz, 1H), 7.98 (d, J=5.0 Hz, 1H), 6.47 (s, 2H).

1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
2. temperatureit was cooled to room temperature
3. concentrationconcentrated to a volume of around 20 mL under reduced pressure
4. filtrationThe resulting suspension was collected by filtration
5. washthe solid was washed with 60:1 dichloromethane/ethanol (50 mL)

ORD record

ord-368ba3583e96420187f3868d868ba434

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921353B2