Iodoethane → HCID 57434154, compound

Temperature

60 °C

3-Bromo-7H-imidazo[1,2-a]pyrazin-8-one (prepared as described in Example 5, 1.6 g, 7 mmol) was suspended in N,N-dimethylformamide (15 ml) then treated with sodium hydride (420 mg of a 60% dispersion in mineral oil, 10.5 mmol). The resulting mixture was heated at 60° C. for 20 min then treated with iodoethane (840 μl, 10.6 mmol). After stirring for 40 min the reaction was cooled, diluted cautiously with water (150 ml) and then extracted with dichloromethane (2×100 ml). The organics were combined, washed with water, dried over anhydrous magnesium sulphate, filtered and concentrated under high vacuum. The residue was triturated with diethyl ether and the resulting solid collected by filtration and recrystallized from ethyl acetate/methanol to furnish 3-bromo-7-ethyl-7H-imidazo[1,2-a]pyrazin-8-one as a white solid (0.34 g): δH (400 MHz, DMSO) 1.23 (3H, t, J 7), 3.94 (2H, q, J 7), 7.31 (1H, d, J 6), 7.41 (1H, d, J 6), 7.62 (1H, s); m/z (ES+) 244 and 242 [M+H]+.

1. temperaturewas cooled
2. extractionextracted with dichloromethane (2×100 ml)
3. washwashed with water
4. dry with materialdried over anhydrous magnesium sulphate
5. filtrationfiltered
6. concentrationconcentrated under high vacuum
7. customThe residue was triturated with diethyl ether
8. filtrationthe resulting solid collected by filtration
9. customrecrystallized from ethyl acetate/methanol

ORD record

ord-300efcbdf11649e8b97975e57363454e

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07485640B2