Triethylamine → HCID 11182227, compound

Participants

Reaction Steps

2.0 g (7.2 mmol) of 6-(diphenylphosphino)-2-aminopyridine from example 14.3.1 were dissolved in 40 ml of dichloromethane and admixed with 1.6 ml (1.2 g, 10.8 mmol) of triethylamine and 0.16 g (0.7 mmol) of 4-dimethylaminopyridine (DMAP). After cooling to 0° C. (H2O/ice), 1.2 ml (1.2 g, 8.8 mmol) of pivaloyl chloride were slowly added dropwise and the mixture was kept at this temperature for 3 h. The mixture was allowed to warm to room temperature overnight and the solvent was then removed under reduced pressure. The residue was purified by filtration together with cyclohexane/ethyl acetate (1:1) through a short silica gel column (3×10 cm). The solvent was removed under reduced pressure and the resulting oil crystallized by digesting with petroleum ether (40/60). The solid was filtered off, washed with petroleum ether (40/60) and dried under reduced pressure. 2.25 g (6.2 mmol, 86.1%) of 6-(diphenylphosphino)-2-pivaloylaminopyridine were obtained as a beige-colored solid.

Provenance & Evidence