Potassium Iodide → N-Isopropyl-N-(4-methoxy-phenyl)-2-[2-(pyrimidin-2-ylamino)-phenylamino]-acetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-pyrimidin-2-yl-benzene-1,2-diamine (82 mg, 0.441 mmol) in DMF (2 mL) was added potassium carbonate (61 mg, 0.441 mmol), potassium iodide (7 mg, 0.044 mmol), and 2-Bromo-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (126 mg, 0.441 mmol). The resultant reaction mixture was stirred overnight at 60° C. The solvent was removed in vacuo and the crude material partitioned between CH2Cl2 (35 mL) and water (15 mL). The organic phase was separated, dried with MgSO4, filtered and concentrated to a yellow oil which upon trituration with EtOH (6 mL) and filtration gave the title compound (96.7 mg, 0.247 mmol) as yellow crystals: 1H NMR (CDCl3, 300 MHz): 8.36 (d, 2H, J=4.9 Hz), 7.38 (dd, 1H, J=1.2, 7.8 Hz), 7.06-6.90 (m, 6H), 6.75 (t, 1H), 6.66 (t, 1H), 6.36 (dd, 1H, J=1.2, 7.8 Hz), 4.97 (m, 1H), 3.87 (s, 3H), 3.43 (s, 2H), 1.04 (d, 6H, J=6.8 Hz); TLC (EtOAc): Rf =0.62; MS (FAB) m/z 392.0 (MH+).

Provenance & Evidence