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

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.

1. stirringthe mixture was stirred for 1 hour
2. filtrationThe mixture was filtered through a pad of celite
3. concentrationThe filtrate was concentrated

ORD record

ord-e32e0480cb8c4a32bb20f6f4b78ae0b9

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06713474B2