Dimethylformamide → HCID 10332062, compound

Participants

Reaction Conditions

Reaction Steps

3-Amino-6-bromo-N-methylpyrazine-2-carboxamide (1.34 g, 5.8 mmol) and 3-hydroxyphenylboronic acid (1.2 g, 8.7 mmol) were taken into DMF (10 mL) followed by addition of [1,1′-bis(diphenylphosphinoferrocene]dichloropalladium (II) dichloromethane complex (440 mg, 0.54 mmol) and triethylamine (4.8 mL, 35 mmol). The mixture was heated to 95° C. for 12 hours then cooled to room temperature and diluted with an excess of ethyl acetate. The organic solution was washed with 0.5 M aqueous hydrochloric acid (1×), water (3×) then brine and dried over anhydrous magnesium sulfate. The mixture was then filtered and the organic solution concentrated and the residue purified by silica gel flash chromatography using ethyl acetate:hexanes (3:1) eluent. The pure fractions were combined and concentrated then dried in vacuo to give 3-amino-6-(3-hydroxyphenyl)-N-methylpyrazine-2-carboxamide (1.01 g, 71% yield) as a yellow solid: MS (EI) for C12H13N4O2: 245 (MH+).

Provenance & Evidence