Cyclopentylamine → N-Cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(3-methoxyphenyl)imidazo[1,2-a]pyridin-8-amine

関与物質

反応条件

反応手順

To a solution of 4-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-3-yl]-N-phenylpyrimidin-2-amine (162 mg, 0.39 mmol) in cyclopentylamine (5 mL) was added, successively, racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (15.3 mg, 0.02 mmol), cesium carbonate (376 mg, 1.15 mmol) and palladium (II) acetate (3.5 mg, 0.015 mmol). The resulting mixture was heated in a sealed tube at 150° C. for 24 hours at which time the reaction was judged complete by thin layer chromatography. The solution was cooled to room temperature and ethyl acetate and water were added. The phases were separated and the organic layer was washed with water and brine. The combined organics were dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (2:1 hexanes-ethyl acetate) to give N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-8-amine (55 mg, 31%) as a white solid. 1H NMR (CDCl3): δ 8.90 (m, 1 H), 8.08 (d, 1 H), 7.37–7.22 (m, 2 H), 6.96 (m, 1 H), 6.79 (t, 1 H), 6.43 (d, 1 H), 6.30 (d, 1 H), 5.40 (d, 1 H), 5.31 (d, 1 H), 4.37 (m, 1 H), 3.94 (m, 1 H), 3.85 (s, 3 H), 2.14–2.07 (m, 4 H), 1.82–1.56 (m, 12 H); MS m/z 469 (M+1).

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