反应详情

A mixture of 5-(4-amino-3-methoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.025 g, 0.08 mmol), benzyl chloroformate (0.016 g, 0.09 mmol), pyridine (0.50 ml) and dichloromethane (0.50 ml) was stirred at room temperature over the weekend and poured into water. The resulting precipitate was collected by filteration and purified by flash column chromatography on silica using ethyl acetate/n-heptane (9:1) as the mobile phase to give benzyl N-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate as a white solid (0.002 g, 0.004 mmol): 1H NMR (DMSO-d6, 400 MHz) δ 8.64 (s, 1H), 8.13 (s, 1H), 7.74 (d, 1H), 7.34-7.45 (m, 6H), 7.10 (d, 1H), 7.02 (dd, 1H), 6.08 (broad, 2H), 5.16 (s, 2H), 5.08 (m, 1H), 3.86 (s, 3H), 2.11 (m, 2H), 1.91 (m, 4H), 1.69 (m, 2H); MH+458; TLC (ethyl acetate) Rf 0.32; RP-HPLC (Hypersil C18, 5 μm, 200 A, 25 cm; 25%-100% acetonitrile-0.1M ammonium acetate over 25 min 1 ml/min) Rt 19.00 min.

1. customThe resulting precipitate was collected by filteration
2. custompurified by flash column chromatography on silica