反应详情

Diethyl 3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanedioate, prepared substantially as described in Example 407 (0.80 g, 0.0016 mol), was dissolved in THF (40 mL, 0.49 mol) and cooled in an ice bath under a nitrogen atmosphere. To this mixture, 1.0 M lithium tetrahydroaluminate in THF (3.2 mL) was added slowly. The reaction was stirred for 1 h, quenched with ice and partitioned between ethyl acetate and 1 N HCl. The organic layer was washed with brine, dried over magnesium sulfate and concentrated to give an amber oil. The product was purified by FCC on silica gel eluting with an ethyl acetate:methanol gradient to give 3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentane-1,5-diol as a clear viscous oil (0.51 gm, 76%), LC/MS (M+H)+: 418, 1H NMR (DMSO-d6) δ, 8.85(s, 1H), 8.41(s, 1H), 8.37(s, 1H), 7.45(d,1H), 6.83(d, 1H), 5.73(s, 2H), 4.91(m, 1H), 3.75(m,2H), 3.59(m, 2H), 3.45(m,2H), 2.18(m, 4H), 0.95(m,2H), 0.1(s, 9H).

1. temperaturecooled in an ice bath under a nitrogen atmosphere
2. customquenched with ice
3. custompartitioned between ethyl acetate and 1 N HCl
4. washThe organic layer was washed with brine
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated
7. customto give an amber oil
8. customThe product was purified by FCC on silica gel eluting with an ethyl acetate