Cesium carbonate → [5-(Benzhydrylidene-amino)-pyridin-3-yl]-[7-bicyclo[1.1.1]pent-1-yl-2-(4-methoxy-benzylamino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-methanone

Participants

Reaction Steps

To a stirred solution of [7-Bicyclo[1.1.1]pent-1-yl-2-(4-methoxy-benzylamino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-(5-bromo-pyridin-3-yl)-methanone (Preparation 285, 1.18 g, 2 mmol) and benzophenoneimine (0.50 mL, 3 mmol) in dry toluene (50 mL), cesium carbonate (3.2 g, 10 mmol) was added and the reaction mixture was purged under N2 for 20 min and then Pd(OAc)2 (45 mg, 0.2 mmol) and BINAP (125 mg, 0.2 mmol) were added followed by degassing for another 10 min and refluxing overnight. The reaction mass was cooled to room temperature and filtered through a pad of Celite. The filtrate was partitioned between water (25 mL) and EtOAc (100 mL). The organic phase was washed with brine (10 mL), dried (Na2SO4) and evaporated in vacuo. Purification by column chromatography on silica gel (EtOAc:Hexane 25:75) afforded the title compound as a yellow solid in 85% yield, 1.1 g.

Provenance & Evidence