Multi-step reaction with 9 steps
1.1: palladium on activated charcoal; methanesulfonic acid; hydrogen; acetic acid / ethanol; ethyl acetate
2.1: potassium hydroxide / methanol; water / 3.5 h / 100 °C
3.1: pyridine; dmap / methanol / 144 h / Heating
4.1: ethyl methyl ether; water / 16 h / 125 °C
5.1: tetrabutyl-ammonium chloride; N,N-dimethyl-aniline; trichlorophosphate / acetonitrile / 8.5 h / 110 °C
5.2: 15.25 h / 0 °C
6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 0.5 h / 20 °C
6.2: 17 h / 70 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2.5 h / 20 °C
8.1: ammonia / methanol / 15 h / 85 °C / Autoclave
9.1: trimethylsilyl bromide / acetonitrile / 16 h / 20 °C
With
pyridine; dmap; methanesulfonic acid; trimethylsilyl bromide; palladium on activated charcoal; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; ammonia; hydrogen; acetic acid; N,N-dimethyl-aniline; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium hydroxide; trichlorophosphate;
In
tetrahydrofuran; methanol; ethanol; ethyl methyl ether; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.ijpharm.2010.06.036