Reaktion #79824

Reaktionsgleichung

Phenyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate

2-morpholino-1-ethanol

→

2-morpholinoethyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed
2. 2
   Sonstigethe residue was purified by preparative reverse phase HPLC

Vorschrift

Phenyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate (25 mg, 0.054 mmol) was mixed with 2-morpholino-1-ethanol (0.1 mL) in pyridine (0.7 mL). The reaction mixture was heated at 100° C. overnight. The solvent was removed and the residue was purified by preparative reverse phase HPLC to give 2-morpholinoethyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate (24 mg, 0.048 mmol). The solid was dissolved in ethyl acetate (2 mL) and 1.0N HCl in ether (0.2 mL) was added slowly. The precipitate was collected through filtration under nitrogen to give 2-morpholinoethyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate hydrochloride (24 mg, 0.045 mmol). 1H NMR (DMSO-d6) δ 1.88(m, 2H), 2.16(m, 2H), 3.55(m, 8H), 3.90(s, 3H), 4.03 (m, 4H), 4.49(m, 2H), 4.92(m, 1H), 7.07(m, 1H), 7.15(s, 1H), 7.65(bs, 2H), 7.84(s, 1H), 8.45(s, 1H), 8.75(s, 1H) 10.95(bs, 1H). LC/MS MH+=497.

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