Toluene → 7-Cyclopent-3-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

N-[(1S)-2,3-Dihydro-1H-inden-1-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (1.32 g, 5.29 mmol) was azeotroped with toluene and placed under high vacuum for 30 min. N,N-Dimethylformamide (17.7 mL) was added, followed by cesium carbonate (1.99 g, 6.10 mmol). The mixture was stirred at 70° C. for 10 min. Cyclopent-3-en-1-yl methanesulfonate (0.660 g, 4.07 mmol) in N,N-dimethylformamide (12.6 mL) was added dropwise. The reaction mixture was heated to 110° C. for 1 h. The reaction mixture was cooled, quenched with brine and diluted with H2O. The aqueous layer was extracted with EtOAc (3×), washed with H2O and brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by via silica gel chromatography, eluting with a gradient of 0 to 5% MeOH in DCM followed by 25 to 50% EtOAc in hexanes, to afford the title compound as a pale brown solid (0.684 g, 53%). LC/MS: Rt=1.38 min, ES+ 317 (FA standard).

Provenance & Evidence