Ammonia → HCID 10290898, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,4-dichloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazine (500 mg, 1.8 mmol), 4-vinylphenylamine (228 mg, 1.9 mmol), tetrahydrofuran (20 ml), and N,N-diisopropylethylamine (0.63 ml, 3.6 mmol) was stirred for 2 hours. The mixture was transferred to a pressure bottle and chilled to −78° C. A slow stream of ammonia gas was passed into the mixture for 2 minutes and the bottle was sealed. After stirring at room temperature for 60 hours, the mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3) to provide the title compound (260 mg, 41% yield). 1H NMR (acetone-d6) 8.78 (br s, 1H), 7.92 (d, J=2.4 Hz, 1H), 7.88 (d, J=8.3 Hz, 2H), 7.44 (d, J=8.6 Hz, 2H), 7.39 (dd, J=2.4 Hz, J=8.2 Hz, 1H), 7.30 (d, J=8.2 Hz, 1H), 6.74 (dd, J=11.0 Hz, J=17.6 Hz, 1H), 6.64 (br s, 1H), 5.73 (dd, J=1.0 Hz, J=17.6 Hz, 1H), 5.15 (dd, J=1.0 Hz, J=11.0 Hz, 1H), 2.61 (s, 3H).

Provenance & Evidence