Dimethylformamide → HCID 67305053, compound

Participants

Reaction Steps

To a solution of 4-(6-methoxy-4-(piperidin-4-ylamino)naphthalen-2-yl)-N-methylpyrimidin-2-amine 150 (0.46 g, 1.32 mmol), N,N-diisopropylethylamine (0.92 mL, 5.2 mmol), N,N-dimethylformamide (2 mL), and tetrahydrofuran (10 mL), (9H-fluoren-9-yl)methyl carbonochloridate (0.41 g, 1.6 mmol) was added. The reaction was stirred at room temperature for 30 min and then partitioned between water (100 mL) and ethyl acetate (200 mL). The aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organics were dried over sodium sulfate, filtered and concentrated (rotary). The residue was purified by column chromatography (silica gel) using 60% ethyl acetate/hexanes as the eluent to afford (9H-fluoren-9-yl)methyl 4-((7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)amino)piperidine-1-carboxylate 205 as a yellow solid (0.53 g). LC/MS (m/z): 586 [M+H].

Provenance & Evidence