1,2-Dimethoxyethane → 5-[2-Methyl-4-(methylthio)phenyl]-2-pyrazinamine

Participants

Reaction Conditions

Reaction Steps

A mixture of [2-methyl-4-(methylthio)phenyl]boronic acid (prepared as in Example 185, Step 2, 253 mg, 1.390 mmol), 5-bromo-2-pyrazinamine (242 mg, 1.390 mmol), Pd(PPh3)2Cl2 (195 mg, 0.278 mmol), DME (5 mL) and 2M Na2CO3 (8 mL) was stirred at 80° C. overnight. The mixture was cooled to ambient temperature, charged with CH2Cl2 and water, and stirred at ambient temperature for 30 min. The mixture was filtered, the organics were separated, and the aqueous layer was washed with CH2Cl2. The organics were pooled, dried over MgSO4, filtered, and the filtrate was concentrated. The crude product was purified by chromatography on a silica gel column using 0 to 50% EtOAc/hexane to give 190 mg (59%) of 5-[2-methyl-4-(methylthio)phenyl]-2-pyrazinamine as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.13 (s, 1H), 8.05 (s, 1H), 7.29 (d, 1H, J=8.5 Hz), 7.17-7.12 (m, 2H), 4.97-4.82 (m, 2H), 2.50 (s, 3H), 2.36 (s, 3H); LRMS (ESI), m/z 232 (M+H).

Provenance & Evidence