Acetic Acid → 7-{4-[2-(4-methylpiperazino)ethyl]cyclohexyl}-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

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Reaction Steps

A mixture of 2-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}acetaldehyde (0.025 g, 0.059 mmol), N-methylpiperazine (0.0083 g, 0.083 mmol) and acetic acid (0.0035 g, 0.059 mmol) in 1,2-dichloroethane (0.4 mL) was stirred for 10 min at ambient temperature and sodium triacetoxyborohydride (0.019 g, 0.089 mmol) was added. The mixture was stirred at ambient temperature under an atmosphere of nitrogen for 6 hours and the solvent removed under reduced to yield a yellow oil. The compound was purified by preparative RP-HPLC to yield 7-{4-[2-(4-methylpiperazino)ethyl]cyclohexyl}-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.016 g, 0.031 mmol) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 8.27(s, 1H), 7.45(d, 2H), 7.37(t, 2H), 7.16(t, 1H), 7.09(m, 5H), 5.57(br, 2H), 4.73(m, 1H), 2.33(s, 3H), 2.49-1.65(m, 19H); 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 8.15 min. MS: MH+ 511.

Provenance & Evidence