Aniline → 2-anilino-6-(2-chlorophenyl)imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one

Participants

Reaction Steps

A mixture of Example 1E (70.0 mg, 0.195 mmol) and aniline (39.1 μl, 0.428 mmol) was heated in a capped vial at 90° C. for 1 hour. After cooling, the residue was treated with saturated NaHCO3/brine and extracted with ethyl acetate (2×). The combined organic layers were dried over MgSO4, filtered, concentrated, and purified on a 12 g column using the ISCO Companion flash system eluting with CH2Cl2/ethyl acetate (8:2 to 7:3) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.08 (d, J=1.83 Hz, 1H), 7.14 (t, J=7.48 Hz, 1H), 7.42 (t, J=7.63 Hz, 2H), 7.54-7.59 (m, 2H), 7.61-7.66 (m, 1H), 7.70-7.74 (m, 1H), 7.79-7.90 (m, 3H), 9.14 (s, 1H), 10.78 (s, 1H). MS (ESI+) m/z 389.2 (M+H)+.

Provenance & Evidence