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

To a solution of 7-methylimidazo[1,2-c]pyrimidine (0.3404 g, 2.56 mmol) in acetic acid (10 ml) was added sodium acetate (0.3132 g, 3.82 mmol), then, dropwise over 7 min, a solution of bromine (66.0 μl, 1.28 mmol) in acetic acid (2 ml). The solution was stirred at room temperature for 20 min, then more bromine (19.7 μl, 0.382 mmol) in acetic acid (0.6 ml) was added over 4 min. The solution was stirred at room temperature for a further 15 min, then partitioned between saturated aqueous NaHCO3 (200 ml) and ethyl acetate (200 ml). The aqueous layer (pH 9) was further extracted with ethyl acetate (200 ml), and the combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, EtOAc) to afford 0.2298 g (42%) of the title compound: 1H NMR (360 MHz, CDCl3) δ 2.57 (3H, s), 7.29 (1H, s), 7.56 (1H, s), 8.91 (1H, s); MS (ES+) m/z 212/214 [M+H]+.

1. stirringThe solution was stirred at room temperature for a further 15 min
2. custompartitioned between saturated aqueous NaHCO3 (200 ml) and ethyl acetate (200 ml)
3. extractionThe aqueous layer (pH 9) was further extracted with ethyl acetate (200 ml)
4. dry with materialthe combined organic extracts were dried (Na2SO4)
5. customevaporated in vacuo
6. customThe residue was purified by flash chromatography (silica gel, EtOAc)

ORD record

ord-32b0d6825932486485e2d5d9e264f995

Source dataset

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06914065B2