N-bromobutanimide → 5-Bromo-6-chloropyrazin-2-amine

Temperature

0 °C

6-Chloropyrazin-2-amine (2.50 g, 19.3 mmol) was stirred in dichloromethane (60 mL) and cooled to 0° C. N-Bromosuccinimide (2.92 g, 16.4 mmol) was added slowly and the reaction mixture was stirred at 0° C. for 60 minutes. The reaction mixture was filtered through celite and concentrated to give a brown oil. Purification by flash chromatography, eluting with 0-25% ethyl acetate-hexane, gave the title compound as a yellow solid (1.69 g, 8.16 mmol, 42%). 1HMR (d6-DMSO, 400 MHz) δ 7.65 (s, 1H), 7.1 (br s, 2H). LC-MS (1) rt 1.46 min; m/z (ESI−) 205 (M−H).

1. filtrationThe reaction mixture was filtered through celite and
2. concentrationconcentrated
3. customto give a brown oil
4. customPurification by flash chromatography
5. washeluting with 0-25% ethyl acetate-hexane

ORD record

ord-66baf1be2be64c5fa2e70dbb03ee932f

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530468B2