Reaction #79874

Reaction equation

water

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

sodium hydroxide

ethanol

→

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

Yield 84.6%

Solvents

acetic acid

Conditions

Workup

1. 1
   Filtrationfiltered through a pad of celite
2. 2
   OtherThe filtrate was evaporated under reduced pressure
3. 3
   Otherto yield a white solid which
4. 4
   Otherto precipitate the product
5. 5
   FiltrationThe suspension was then filtered

Procedure

A mixture of 2-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyliden}acetic acid (0.60 g, 1.36 mmol), 10% palladium on activated carbon (0.18 g), 1M aqueous sodium hydroxide (9 mL) and ethanol (60 mL) was hydrogenated under an atmosphere of hydrogen (60 psi) for 20 hours and filtered through a pad of celite. The filtrate was evaporated under reduced pressure to yield a white solid which was taken into water (20 mL) followed by addition of 1M acetic acid (20 mL) to precipitate the product. The suspension was then filtered and the solid was lyophilized to yield 2-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}acetic acid (0.51 g, 1.15 mmol) as a white solid: 1H NMR (DMSO-d6, 400 MHz) δ 11.99(br, 1H), 8.13(s, 1H), 7.60 (s, 1H), 7.49(d, 2H), 7.41(t, 2H), 7.15(t, 1H), 7.09(m, 4H), 6.09(br, 2H), 4.60 (m, 1H), 2.20-1.24(m, 11H); RP-HPLC (Hypersil C18, 5 μm, 100 A, 250×4.6 mm; 25%-100% acetonitrile-0.05M ammonium acetate over 10 min, 1 mL/min) Rt 9.62 min. MS: MH+ 443.

Source