Cesium carbonate → HCID 86672112, compound

Participants

Reaction Steps

A mixture of (5-((Diphenylmethylene)amino)pyridin-3-yl)(7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone (Preparation 195, 1120 mg, 2.77 mmol) and Cs2CO3 (2710 mg, 8.31 mmol) in DMF (10 mL) was stirred at room temperature for 30 min. A solution of crude 2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-6-yl trifluoromethanesulfonate (Preparation 108) in DMF (3.8 mL) was then added to the reaction and the resulting mixture stirred at room temperature for 16 hours. The reaction was quenched with saturated aqueous ammonium chloride solution (100 mL) and the mixture extracted with EtOAc (100 mL×3). The combined organic layers were washed with water (200 mL), dried over sodium sulfate and concentrated in vacuo. The resulting material was purified by column chromatography on silica gel (gradient of heptane:EtOAc 100:0 to 50:50) to provide (5-((diphenylmethylene)amino)pyridin-3-yl)(7-(2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-6-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone.

Provenance & Evidence