Tributylstannane → N-((S)-2,3-dihydro-1H-inden-1-yl)-7-((4aS,6R,7aS)-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-6-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

O-[(4aS,6R,7S,7aR)-6-{4-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo-[2,3-d]pyrimidin-7-yl}-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-7-yl] O-phenyl thiocarbonate (5.00 g, 7.88 mmol) was dissolved in toluene (150. mL) under an atmosphere of nitrogen and tri-n-butyltin hydride (4.24 mL, 15.8 mmol) was added followed by 2,2′-azo-bis-isobutyronitrile (259 mg, 1.58 mmol). The solution was heated to reflux for 30 min, the mixture was cooled down, the solvent was concentrated to 30 mL and the residue was purified via silica gel chromatography eluting with a gradient of 30 to 100% EtOAc in hexanes to afford the title compound (3.00 g, 79%). LC/MS: Rt=2.12 min, ES+ 483 (AA standard).

1. temperatureThe solution was heated
2. temperatureto reflux for 30 min
3. temperaturethe mixture was cooled down
4. concentrationthe solvent was concentrated to 30 mL
5. customthe residue was purified via silica gel chromatography
6. washeluting with a gradient of 30 to 100% EtOAc in hexanes

ORD-Eintrag

ord-3bc8248277444a6691de41966f0a41b8

Quelldatensatz

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08207177B2