6-tert-Butylpyridin-2-amine → HCID 86699095, compound

Participants

Reaction Steps

A mixture of tert-butyl {(1S)-1-[(benzyloxy)methyl]-3-bromo-2-oxopropyl}carbamate (3.72 g, 10.0 mmol) and 2-amino-6-tert-butylpyridine (1.5 g, 10.0 mmol) in toluene (50 mL) was stirred at room temperature for 14 hours and then refluxed for 5 hours. The reaction mixture was cooled and concentrated in vacuo. The crude product was purified by silica gel column chromatography eluting with 30% EtOAc in petroleum ether. The residue was treated with cold conc. HCl (5 mL) at 0° C. followed by stirring at room temperature for 18 hours. The reaction mixture was basified with saturated aqueous Na2CO3 solution, extracted with EtOAc, dried over Na2SO4 and concentrated in vacuo to afford a residue which was purified further by preparative TLC eluting with 20% MeOH in EtOAc to afford the title compound (21 mg, 25%).

Provenance & Evidence