(Diethylamino)sulfur trifluoride → 7-(1-Fluoro-1-methylethyl)imidazo[1,2-alpha]pyrimidine

Temperature

-78 °C

To a cooled (−78° C.) suspension of 2-(imidazo[1,2-α]pyrimidin-7-yl)propan-2-ol (1.02 mg, 5.8 mmol) in dichloromethane (25 ml) was added (diethylamino)sulfur trifluoride (1.22 mg, 7.5 mmol) dropwise over 5 min. The mixture was stirred at −78° C. for 40 min then quenched with methanol (1 ml). The mixture was warmed to ambient temperature, made basic with saturated sodium hydrogencarbonate solution (25 ml) and extracted with dichloromethane (2×25 ml). The combined organics were washed with brine (50 ml), dried over anhydrous sodium sulfate and evaporated to dryness. Purification of this material by chromatography on silica eluting with dichloromethane (containing 0.5% conc. ammonia) on a gradient of methanol (1-3%) gave 7-(1-fluoro-1-methylethyl)imidazo[1,2-α]pyrimidine (180 mg, 17%) as a yellow solid: δH (360 MHz, CDCl3) 1.78 (6H, d, J 22), 7.21 (1H, dd, J 7 and 1), 7.54 (1H, d, J 1), 7.79 (1H, d, J 1), 8.45 (1H, d, J 7).

1. temperatureTo a cooled
2. customthen quenched with methanol (1 ml)
3. temperatureThe mixture was warmed to ambient temperature
4. extractionextracted with dichloromethane (2×25 ml)
5. washThe combined organics were washed with brine (50 ml)
6. dry with materialdried over anhydrous sodium sulfate
7. customevaporated to dryness
8. customPurification of this material by chromatography on silica eluting with dichloromethane (containing 0.5% conc. ammonia) on a gradient of methanol (1-3%)

ORD record

ord-ce9f368ff30648a195edbe60a2739912

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06900215B2