反应详情

To a solution of N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-7-amine (1.16 g, 2.48 mmol) in dichloromethane (50 mL) at −78° C. was added boron tribromide (9.92 mL, 1.0 M in dichloromethane, 9.92 mmol) dropwise. The resulting solution was allowed to warm to room temperature. After stirring for 15 hours at room temperature, the mixture was cooled to 0° C. and quenched by the addition of water. The mixture was extracted with ethyl acetate. The organic phase was dried (magnesium sulfate), filtered and concentrated to give a solid residue which was purified by flash chromatography (95:5 chloroform-methanol). 4-{7-(Cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenol was obtained as a yellow solid (0.80 g, 71%). 1H NMR (CDCl3): δ 7.91 (d, 1H), 7.70 (d, 1H), 7.46 (d, 2H), 7.26 (t, 1H), 6.86 (d, 2H), 6.27 (d, 1H), 6.00–5.97 (m, 2H), 5.06 (d, 1H), 4.33 (m, 1H), 3.96 (m, 1H), 2.10–2.03 (m, 4H), 1.78–1.47 (m, 12H); MS m/z 455 (M+1). U157430-190

1. temperaturethe mixture was cooled to 0° C.
2. customquenched by the addition of water
3. extractionThe mixture was extracted with ethyl acetate
4. dry with materialThe organic phase was dried (magnesium sulfate)
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a solid residue which
8. customwas purified by flash chromatography (95:5 chloroform-methanol)