Bromine → 3-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine

7-Trifluoromethylimidazo[1,2-α]pyrimidine (20. g, 10.7 mmol) and sodium acetate (1.1 mg, 13.4 mmol) were dissolved in methanol (30 ml) which had been saturated with potassium bromide and this mixture was cooled to −10° C. before dropwise addition of bromine (1.86 mg, 11.7 mmol) over 5 min. On complete addition the mixture was quenched by addition of 1M sodium sulfite solution (2 ml) and the solvent removed in vacuo. The residue was treated with water (100 ml) and saturated sodium hydrogencarbonate solution (100 ml) and extracted with ethyl acetate (3×100 ml). The organics were combined then washed with brine (100 ml), dried over anhydrous sodium sulfate and evaporated to give an off-white solid. This solid was purified by silica gel chromatography eluting with dichloromethane and 1% conc. ammonia on a gradient of methanol (1-2%) to give 3-bromo-7-trifluoromethylimidazo[1,2-α]pyrimidine (1.98 g) as a white solid: δH (400 MHz, CDCl3) 7.35 (1H, d, J 7), 8.02 (1H, s), 8.62 (1H, d, J 7).

1. additionOn complete addition the mixture
2. customwas quenched by addition of 1M sodium sulfite solution (2 ml)
3. customthe solvent removed in vacuo
4. additionThe residue was treated with water (100 ml) and saturated sodium hydrogencarbonate solution (100 ml)
5. extractionextracted with ethyl acetate (3×100 ml)
6. washThe organics were combined then washed with brine (100 ml)
7. dry with materialdried over anhydrous sodium sulfate
8. customevaporated
9. customto give an off-white solid
10. customThis solid was purified by silica gel chromatography
11. washeluting with dichloromethane and 1% conc. ammonia on a gradient of methanol (1-2%)

ORD record

ord-05f68012eb4d417d8c7db74f136917a4

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07030128B2