Water → HCID 67354691, compound

Participants

Reaction Steps

To a stirred solution containing 2.76 g (13.75 mmol) of 2-amino-5-bromo-4,6-dimethylpyridine (13) in 25 mL of toluene were added 2.02 mL (17.18 mmol) of 2,5-hexadienone followed by 130 mg (0.68 mmol) of p-toluene sulfonic acid. The reaction mixture was stirred at reflux overnight under argon atmosphere. The reaction mixture was poured into 150 mL of water and then extracted with a portion of 200 mL of ethyl acetate. The organic solution was washed with a portion of 150 mL of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with hexanes-ethyl acetate 5:1 gave the expected product as an orange oil: yield 2.37 g (62%). 1H-NMR (CDCl3) δ 6.93 (s, 1H), 5.88 (s, 2H), 2.70 (s, 3H), 2.47 (s, 3H), 2.12 (s, 6H); 13C-NMR (CDCl3) δ 157.35, 149.32, 128.42, 122.49, 121.22, 25.58, 23.41, 13.10.

Provenance & Evidence