Benzenamine, 4-(4-morpholinyl)- → 2-(4-Morpholinophenylamino)-6-(3-acetamidophenyl)pyrazine

Participants

Reaction Steps

Using Method O, 2-(3-acetamidophenyl)-6-chloropyrazine (150 mg, 0.61 mmol), 4-morpholinoaniline (155.4 mg, 0.87 mmol), tris(dibenzylideneacetone) dipalladium (0) (28 mg, 0.030 mmol), 1,3-bis(2,6-di-1-propylphenyl)-4,5-dihydro-imidazolium tetrafluoroborate (29 mg, 0.061 mmol), potassium tert-butoxide (102 mg, 0.91 mmol), and dioxane (3.5 mL) were reacted at 100° C. for 30 minutes with microwave heating. The reaction crude was passed through a short silica gel column (2 g silica), which was thoroughly washed with ethyl acetate. The last fractions of this column were collected to give 9 mg of pure title compound. The first fractions were collected, the solvent was evaporated under vacuo and the resulting solid was crystallised in ethyl acetate to produce 61 mg of the title compound. Yield: 29.8%. 1H NMR (250 MHz, DMSO-d6) δ 2.09 (s, 3 H), 3.03-3.07 (bt, 4 H), 3.72-3.76 (bt, 4 H), 6.97 (d, 2 H, J=9.0 Hz), 7.42 (t, 1 H, J=7.9 Hz), 7.65-7.68 (m, 2 H), 7.70 (d, 2H, J=8.9 Hz), 8.11 (s; 1 H), 8.33 (bs, 2 H), 9.36 (s, 1 H), 10.09 (s, 1 H); 13C NMR (62.9 MHZ, DMSO-d6) δ 24.11, 49.24, 66.16, 116.01, 117.08, 119.61, 119.89, 121.08, 129.16, 133.03, 133.15, 137.23, 139.87, 146.10, 147.95, 151.70, 168.45; m/z 390.2 [(M+H)+, calcd for C22H23N5O2 389.2].

Provenance & Evidence