3,4,5-Trimethoxyaniline → 2-(3,4,5-Trimethoxyphenylamino)-6-(2-chlorophenyl-oxy)-pyrazine

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Using Method EE with 2-chloro-6-(2-chlorophenyloxy)-pyrazine (200 mg, 0.83 mmol) and 3,4,5-trimethoxyaniline (183 mg, 1.00 mmol), and purification by column chromatography (AcOEt:cyclohexane, 1:1), the title compound was obtained (227 mg). Yield: 71%. 1H NMR (250 MHz, DMSO-d6) δ 3.43 (s, 6H, [CH3O]3+5), 3.54 (s, 3H, [CH3O]4), 6.68 (s, 2H, Harom2′+6′), 7.26-7.30 (m, 1H, Harom 4), 7.37-7.40 (m, 2H, Harom 5+6), 7.59 (d, 1H, Harom 3, J=7.8 Hz), 7.82 (s, 1H, HPz 5), 7.95 (s, 1H, HPz 3), 9.56 (s, 1H, NH). m/z: 388.1 [(M+H)+, calcd for C19H18ClN3O4 387.1].

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