反应详情

To a cold (−78° C.) solution of formed N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-8-amine (42 mg, 0.09 mmol) in dichloromethane (5 mL) was added boron tribromide (0.5 mL, 1 M in dichloromethane, 0.5 mmol) dropwise. The solution was allowed to warm to room temperature over 4 hours and stirred for an additional 16 hours. The reaction was quenched by the addition of methanol followed by saturated aqueous sodium bicarbonate. Ether was added and the layers separated. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics were dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (1:1 hexanes:ethyl acetate) provided 3-{8-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]imidazo[1,2-α]pyridin-2-yl}phenol (30 mg, 73%) as a yellow solid. 1H NMR (CDCl3): δ 8.90 (broad, 1H), 7.96 (d, 1H), 7.31 (s, 1H), 7.17 (t, 1H), 7.01 (d, 1H), 6.81–6.75 (m, 2H), 6.38 (d, 1H), 6.27 (d, 1H), 5.53 (d, 1H), 5.28 (d, 1H), 4.30 (m, 1H), 3.88 (m, 1H), 2.10–1.93 (m, 4H), 1.78–1.48 (m, 12H); MS m/z 455 (M+1).

1. customThe reaction was quenched by the addition of methanol
2. additionEther was added
3. customthe layers separated
4. washThe organic layer was washed with brine
5. extractionThe aqueous layer was extracted with ether
6. dry with materialthe combined organics were dried over magnesium sulfate
7. filtrationFiltration and concentration