4-Chloro-N-methylbenzenamine → HCID 9925034, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2-yl-amine (106 mg, 0.42 mmol), (4-chloro-phenyl)-methyl-amine (0.15 ml, 1.25 mmol), tetrahydrofuran (5 ml), and diisopropylethylamine (0.75 ml, 4.2 mmol) was heated at 40° C. for 72 hours. The mixture was concentrated under reduced pressure and the residue was dissolved in dichloromethane (25 ml). The solution was washed with hydrochloric acid (1 M, 25 ml) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 2% methanol-dichloromethane followed by 5% methanol-dichloromethane. Recrystallization (ethyl acetate-hexane) provided the title compound (33 mg, 22% yield). 1H NMR (DMSO-d6) 7.78 (s, 1H), 7.37-7.46 (m, 4H), 7.26 (d, J=8.4 Hz, 1H), 7.10 (br s, 2H), 3.43 (s, 3H), 2.37 (s, 3H).

Provenance & Evidence