HCID 67305053, compound → HCID 136367448, compound

Participants

Reaction Conditions

Reaction Steps

A round-bottom flask equipped with rubber septum containing solution of (9H-fluoren-9-yl)methyl 4-((7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)amino)piperidine-1-carboxylate 205 (0.41 g, 0.69 mmol) in chloroform (10 mL) was cooled to 0° C. Trifluoroborane dimethylsulfide complex (0.73 mL, 27.7 mmol) was added dropwise via syringe. The reaction mixture was stirred at 0° C. for 5 minutes and allowed to warm to room temperature overnight. The reaction mixture was partitioned between water (100 mL) and ethyl acetate (200 mL). The organic layer was extracted with saturated aqueous sodium bicarbonate (100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated (rotary) to afford a brown solid (0.34 g). The crude compound was purified by column chromatography (silica gel) using 3.5% methanol/chloroform as the eluent and triturated with diethyl ether to afford 9H-fluoren-9-ylmethyl 4-({7-hydroxy-3-[2-(methylamino)pyrimidin-4-yl]-1-naphthyl}amino)piperidine-1-carboxylate 206 as an orange-yellow solid (0.28 g). LC/MS (m/z): 573 [M+H].

Provenance & Evidence