6-tert-Butylpyridin-2-amine → HCID 86689772, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 4,6-dichloropyridazine-3-carboxylate (0.73 g, 3.3 mmol) and 6-tert-butylpyridin-2-amine (992 mg, 6.61 mmol, available commercially from J&W PharmLab, LLC) was dissolved in acetonitrile (3.00 mL) and heated at 130° C. for 20 h. After cooling to room temperature, the mixture was concentrated and the residue purified by flash chromatography (spherical silica 20-45 μM, 50 g, Versaflash Supelco) eluting with 0 to 20% acetone in dichloromethane over 20 min to give ethyl 4-(6-tert-butylpyridin-2-ylamino)-6-chloropyridazine-3-carboxylate (539 mg, 48.7% yield) as a light brown residue. 1H NMR (CHLOROFORM-d) δ: 10.59 (s, 1H), 9.32 (s, 1H), 7.55 (t, J=7.9 Hz, 1H), 6.98 (d, J=7.2 Hz, 1H), 6.66 (d, J=7.9 Hz, 1H), 4.48 (q, J=7.2 Hz, 2H), 1.43 (t, J=7.2 Hz, 3H), 1.28-1.35 (m, 9H); LC-MS 335.0, 337.0 [M+H]+.

Provenance & Evidence