Corey-hopkins reagent → 7-[(1R,4R)-4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)cyclopent-2-en-1-yl]-N-[(1S)-2,3-dihydro-1H-inden-1-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of (3aR,4S,6R,6aS)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-6-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}tetrahydro-3aH-cyclopenta[d][1,3]dioxole-2-thione (138 mg, 0.257 mmol) in THF (0.860 mL) at 0° C. under an atmosphere of nitrogen was added 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine (0.147 mL, 0.793 mmol) dropwise. The solution was stirred for 10 min at 0° C. and then at rt for 5 h. The solvent was removed and the residue was purified by silica gel chromatography eluting with a gradient of 0 to 20% EtOAc in hexanes to afford the title compound as a clear oil (˜70% purity, 81.9 mg, 48%). LC/MS: Rt=2.10 min, ES+ 462 (FA standard).

Provenance & Evidence