3,4,5-Trimethoxyaniline → HCID 58711925, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 1-[3-(methylsulfonyl)-1,2,4-triazin-6-yl]ethylcarbamate (Intermediate 7) (2.0 g, 6.5 mmol) in tetrahydrofuran (50 mL) was added 3,4,5-trimethoxyaniline (1.8 g, 9.7 mmol) and 4-toluenesulfonic acid monohydrate (60 mg). After stirring for 24 hours, silica gel (10 g) was added to the solution, followed by evaporation of the volatiles under reduced pressure. The pre-adsorbed solids were loaded into a solid loading cartridge and subjected to a gradient elution using ethyl acetate:hexane (20:80) to ethyl acetate:hexanes (50:50) using a RediSep silica gel cartridge (40 g; ISCO). The appropriate fractions were combined and concentrated under reduced pressure to give tert-butyl 1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethylcarbamate (1.3 g) as a white solid. 1H NMR (CDCl3): δ8.30 (s, 1H), 7.49 (br, 1H), 6.95 (s, 2H), 5.40-5.30 (m, 1H), 5.00-4.83 (m, 1H), 3.89 (s, 6H), 3.84 (s, 3H), 1.58 (d, J=7.0 Hz, 3H), 1.43 (s, 9H). MS m/z 406 (M+1).

Provenance & Evidence