5-BroMo-3-Methylpyrazin-2-ol synthesis

Yield:100047-56-1 77%

Reaction Conditions:

with N-Bromosuccinimide in N,N-dimethyl-formamide at 0 - 20;

Steps:

1.115.A
To a solution of 3-methylpyrazin-2-ol (1.5 g, 13.62 mmol) in anhydrous DMF (20 mL) was added N-bromosuccinimide (2.67 g, 14.98 mmol) at 0 °C. The reaction mixture was slowly warmed to room temperature and stirred overnight. The resulting mixture was poured into water, and extracted with IPA/DCM (1/5). The combined organics were dried over anhydrous Na₂S0₄, filtered then concentrated. The residue was purified by column chomatography with 80% ethyl acetate/hexanes to give the title compound as white solid (1.97 g, 10.42 mmol, 77% yield).Exact mass calculated for C₅H₅BrN₂0: 188.0, found: LCMS m/z = 189.0 [M+H]⁺; ^lU NMR (400 MHz, DMSO-i ) δ ppm 2.27 (d, J = 0.5 Hz, 3H), 7.73 (s, 1H), 12.3 (s, 1H).

References:

ARENA PHARMACEUTICALS, INC.;JONES, Robert M.;HAN, Sangdon;BUZARD, Daniel J.;LEHMANN, Juerg;NARAYANAN, Sanju;YUE, Dawei WO2011/127051, 2011, A1 Location in patent:Page/Page column 205

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