Tributylstannane → 4-(Benzylsulfanyl)-7-[(4aS,6R,7aS)-2-(4-methoxyphenyl)hexahydrocyclopenta[d]-[1,31dioxin-6-yl]-7H-pyrrolo[2,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a solution of O-[(4aS,6R,7S,7aR)-6-[4-(benzylsulfanyl)-7H-pyrrolo[2,3-d]-pyrimidin-7-yl]-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-7-yl] O-phenyl thiocarbonate (1.77 g, 1.98 mmol) in toluene (91.0 mL) was added 2,2′-azo-bis-isobutyronitrile (67.7 mg, 0.404 mmol) and tri-n-butyltin hydride (1.11 mL, 4.00 mmol) under an atmosphere of nitrogen. The yellow solution was heated to reflux at 140° C. After 2 h, the reaction mixture was cooled, silica gel was added, and the solvent was removed in vacuo. Silica gel chromatography eluting with a gradient of 0 to 100% EtOAc in hexanes afforded the title compound as a semi-solid (800 mg, 85%). LC/MS: Rt=2.38 min, ES+ 475 (FA standard).

Provenance & Evidence