Reaktion #69222

Reaktionsgleichung

Diethyl 3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanedioate

lithium tetrahydroaluminate

→

3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentane-1,5-diol

Ausbeute 76.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled in an ice bath under a nitrogen atmosphere
2. 2
   Sonstigequenched with ice
3. 3
   Sonstigepartitioned between ethyl acetate and 1 N HCl
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Einengenconcentrated
7. 7
   Sonstigeto give an amber oil
8. 8
   SonstigeThe product was purified by FCC on silica gel eluting with an ethyl acetate

Vorschrift

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).

Quelle