p-Toluidine → 6-(2-chlorophenyl)-2-[(4-methylphenyl)amino]imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one

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Reaction Steps

A mixture of Example 1E (132.0 mg, 0.367 mmol) and p-toluidine (86 mg, 0.807 mmol) was heated in a capped vial at 90° C. for 1 hour. After cooling, the residue was treated with saturated aqueous NaHCO3 and brine and extracted with ethyl acetate (twice). 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, CDCl3) δ 2.39 (s, 3H), 7.08 (d, J=1.8 Hz, 1H), 7.26-7.23 (m, 2H), 7.49-7.47 (m, 3H), 7.57-7.55 (m, 2H), 7.66-7.61 (m, 1H), 7.72-7.67 (m, 1H), 7.88-7.72 (m, 1H), 9.24 (s, 1H). MS (ESI+) m/z 403.2 (M+H)+.

Provenance & Evidence