1,2-Dimethoxyethane → 4-tert-Butyl-N-{3-[6-(4-formyl-phenylamino)-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-methyl-phenyl}-benzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(6-Bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-benzaldehyde (3) (2.0 g; 6.51 mmol), 4-tert-butyl-N-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (3.28 g; 7.8 mmol), tetrakis(triphenylphosphine)palladium (0.75 g; 0.65 mmol), 1N sodium carbonate (16.0 mL), and 1,2-dimethoxyethane (50 mL) was heated at 95° C. in a sealed pressure vessel for 12 hr. The mixture was cooled to room temperature, treated with water (70 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with water (2×75 mL) and brine (1×75 mL), dried over solid sodium sulfate, and evaporated under reduced pressure. The resulting residue was triturated with diethyl ether/dichloromethane to give 4-tert-butyl-N-{3-[6-(4-formyl-phenylamino)-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-methyl-phenyl}-benzamide (4) as a light gray solid (3.6 g), MS 495.35 (M+H).

Provenance & Evidence