Bromine → 3-Bromo-7-methylimidazo[1,2-a]pyrimidine

7-Methylimidazo[1,2-a]pyrimidine (100 mg, 0.75 mmol) and sodium acetate (74 mg, 0.90 mmol) were dissolved in methanol (2 ml) which had been saturated with potassium bromide and this mixture was cooled to −10° C. before dropwise addition of bromine (132 mg, 0.83 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 (15 ml) and saturated sodium hydrogencarbonate solution (15 ml) and extracted with ethyl acetate (3×40 ml). The organics were combined then washed with brine (40 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-methylimidazo[1,2-a]pyrimidine (100 mg, 63%) as a white crystalline solid: δH (400 MHz, CDCl3) 2.67 (3H, s), 6.87 (1H, d, J 7), 7.71 (1H, s), 8.27 (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 (15 ml) and saturated sodium hydrogencarbonate solution (15 ml)
5. extractionextracted with ethyl acetate (3×40 ml)
6. washThe organics were combined then washed with brine (40 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-75fdc91a0f444d2191ac6562ef89bd33

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06642229B2