Reaction #79875

Reaction equation

sodium hydroxide

2-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}acetic acid

lithium aluminum hydride

water

Water

→

2-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}-1-ethanol

Yield 82.4%

Solvents

Tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred for 1 hour
2. 2
   FiltrationThe mixture was filtered through a pad of celite
3. 3
   ConcentrationThe filtrate was concentrated

Procedure

A mixture of 2-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}acetic acid (0.23 g, 0.51 mmol) and lithium aluminum hydride (0.30 g, 7.89 mmol) in tetrahydrofuran (25 mL) was stirred at ambient temperature overnight. Water (3 mL) was added followed by 15% aqueous sodium hydroxide (3.5 mL) and water (10.5 mL). Tetrahydrofuran (25 mL) was added and the mixture was stirred for 1 hour. The mixture was filtered through a pad of celite. The filtrate was concentrated and lyophilized to yield 2-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}-1-ethanol (0.18 g, 0.42 mmol) as a white solid: 1H NMR (DMSO-d6, 400 MHz) δ 8.13(s, 1H), 7.51(s, 1H), 7.48 (d, 2H), 7.42(t, 2H), 7.16(t, 1H), 7.09(m, 4H), 6.10(br, 2H), 4.57(m, 1H), 4.36 (t, 1H), 3.47(q, 2H), 2.70-1.65(m, 10H); RP-HPLC (Hypersil C18, 5 μm, 100 A, 250×4.6 mm; 25%-100% over 10 min then 100%-25% over 2 min acetonitrile-0.05M ammonium acetate, 1 mL/min) Rt 10.28 min. MS: MH+ 429.

Source