Dimethylamine → 2-{4-[4-(2-Dimethylaminoacetyl)piperazin-1-yl]anilino}-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine

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Reaction Steps

Chloroacetyl chloride (50 μl, 0.65 mmol) was added dropwise to a stirred solution of 2-[4-(piperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine (Example 20; 200 mg, 0.53 mmol) and triethylamine (90 μl, 0.65 mmol) in DCM (5 ml) at room temperature. After 50 minutes, 2M dimethylamine in THF solution (2 ml, 4 mmol) was added and the reaction was stirred for 5 hours before evaporating under reduced pressure. Chromatography on neutral alumina (activity II) with MeOH:DCM (1:99 to 3:97) gave material which required further purification on silica gel with MeOH:DCM:7N NH3MeOH (3:97:0.0025 to 10:90:0.0025) to give the title compound as a yellow foam. (150 mg 60% yield). NMR: 1.39 (d, 6H), 2.19 (s, 6H), 2.46 (s, 3H), 3.02 (b t, 2H), 3.06 (b t, 2H), 3.59 (b t, 2H), 3.68 (b t, 2H), 5.69 (septuplet, 1H), 6.92 (d, 2H), 6.94 (d, 1H), 7.39 (s, 1H), 7.47 (d, 2H), 8.31 (d, 1H), 9.17 (s, 1H); m/z 463.

Provenance & Evidence