Triethylamine → 2-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}ethyl methanesulfonate

Methanesulfonyl chloride (0.036 g, 0.31 mmol) was added into a solution of 2-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}-1-ethanol (0.11 g, 0.26 mmol) and triethylamine (2.5 mL) in dichloromethane (2.5 mL) at 0° C. The mixture was allowed to warm up to ambient temperature and stirred overnight. Methanesulfonyl chloride (0.036 g, 0.31 mmol) and dichloromethane (2.5 mL) was added. The mixture was stirred at ambient temperature for 17 hours. Methanesulfonyl chloride (0.036 g, 0.31 mmol) and dichloromethane (2.5 mL) was added. The mixture was stirred at ambient temperature for 4 hours. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel using methanol/dichloromethane (5:95) as a mobile phase to yield 2-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}ethyl methanesulfonate (0.10 g, 0.21 mmol) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 8.31(s, 1H), 7.44 (d, 2H), 7.38(t, 2H), 7.15(t, 1H), 7.08 (m, 5H), 5.31(br, 2H), 4.73(m, 1H), 4.32(t, 2H), 3.03(s, 3H), 1.99-1.61(m, 11H); TLC (methanol/dichloromethane=5:95) Rf 0.37; RP-HPLC (Hypersil C18, 5 μm, 100 A, 250×4.6mm; 25%-100% over 10 min then 100%-25% over 2 min acetonitrile-0.05M ammonium acetate, 1 mL/min) Rt 11.45 min; MS: MH+ 507.

1. stirringThe mixture was stirred at ambient temperature for 17 hours
2. stirringThe mixture was stirred at ambient temperature for 4 hours
3. customThe solvent was removed under reduced pressure
4. customthe residue was purified by flash chromatography on silica gel

ORD 기록

ord-7345937f56bd4cfda60054af377090b6

출처 데이터셋

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06713474B2