Benzylamine → Benzyl-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-amine

Participants

Reaction Conditions

Reaction Steps

The mixture of 3-(2-methanesulfonyl-pyrimidin-4-yl)-8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazine (from Example 46 supra) (150 mg, 0.402 mmol) and benzylamine (51.7 mg, 0.482 mmol) was heated at 140° C. with stirring for 2 hours. The resulting oil was purified by chromatography (silica gel, 10 g, 200˜300 mesh, eluting with dichloromethane:methanol, 30:1 to 10:1) to afford the crude product which was purified by prep-HPLC and concentrated to afford benzyl-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-amine (Yield 25 mg, 15.5%). 1H NMR (300 MHz, CDCl3): δ 8.71 (brs, 1H), 8.31 (d, 1H, J=4.8 Hz), 8.04 (s, 1H), 7.42-7.28 (m, 5H), 6.94 (d, 1H, J=5.4 Hz), 5.68 (brs, 1H), 4.71 (d, 2H, J=5.7 Hz), 4.24 (brs, 4H), 2.60-2.57 (m, 4 H), 2.36 (s, 3H). LC-MS: [M+H]+ 401.

Provenance & Evidence