Water → HCID 10355149, compound

Participants

Reaction Conditions

Reaction Steps

3-Amino-6-bromo-N-methylpyrazine-2-carboxamide (2.00 g, 8.65 mmol) was dissolved in DMF followed by addition of 3-hydroxymethyl phenyl boronic acid (1.57 g, 10.32 mmol), K2CO3 (3.0 g, 21.7 mmol) and Pd(PPh3)4 (10 mol %, 1.0 g). This mixture was stirred at 90° C. under nitrogen for 12 hours. The reaction mixture was poured into water (150 mL), and extracted with ethyl acetate (3×50 mL). The organic layers were washed with brine (50 mL) then dried over anhydrous sodium sulfate. Filteration, concentration and column chromatography on silica (50% ethylacetate/hexanes) gave a solid which was dried to afforded 2.02 g (92% yield) of the title compound; 1H NMR (400 MHz, d6-DMSO): δ0 8.80 (s, 1H), 8.74 (br, 1H), 8.01(s, 2H), 7.45 (m, 4H), 5.21(t, 1H), 4.60 (d, 2H), 2.81(d, 3H); MS (EI) for C13H14N4O2: 259.38 (MH+).

Provenance & Evidence