Triphenylphosphine → HCID 86612256, compound

Participants

Reaction Conditions

Reaction Steps

Triphenylphosphine (0.845 g, 3.22 mmol, 1.1 eq), 4-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)butan-1-ol (0.81 g, 2.93 mmol), and tert-butyl N-(tert-butoxycarbonyloxy)carbamate (0.751 g, 3.22 mmol) were dissolved in DMF and cooled to 0° C. Diisopropyl azodicarboxylate (0.634 mL, 3.22 mmol) was added dropwise over 10 minutes to the reaction mixture and was allowed to warm to ambient temperature and stirred overnight. Analysis by HPLC indicated the reaction was incomplete. An additional amount of reagents (0.5 eq) were added to the reaction mixture (cooled to 0° C. before addition of the diisopropyl azodicarboxylate) and stirred for an additional 2 hours. The reaction mixture was concentrated under reduced pressure, dissolved in ethyl acetate (150 mL), washed with a water and brine mixture (1:1, 4×30 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on a BIOTAGE HORIZON High-Performance Flash Chromatography instrument (silica gel, eluting with 2-30% CMA in chloroform) and concentrated under reduced pressure to provide 1.19 g of tert-butyl 4-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl[(tert-butoxycarbonyl)oxy]carbamate.

Provenance & Evidence