2,4-Dimethoxybenzylamine → 4-(4-aminonaphthalen-1-ylthio)-N-(2,4-dimethoxybenzyl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(2-chloropyridin-4-ylthio)naphthalen-1-amine (1.40 g, 90% purity, 4.40 mmol) and (2,4-dimethoxyphenyl)methanamine (3.7 mL, 24 mmol) was heated together at 120° C. for 24 hr. The reaction mixture was loaded directly onto silica and purified by flash column chromatography (SiO2, 80 g, EtOAc in isohexane, 30-70%, gradient elution) to afford 4-(4-aminonaphthalen-1-ylthio)-N-(2,4-dimethoxybenzyl)pyridin-2-amine as a dark red oil (710 mg, 37%); Rt 1.74 min (Method 2); m/z 418 (M+H)+ (ES+).

Provenance & Evidence