Multi-step reaction with 8 steps
1.1: diisopropylamine; n-butyllithium / hexane; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
1.2: -78 - 25 °C
2.1: diisopropylamine; n-butyllithium / hexane; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrahydrofuran / -78 - 25 °C / Inert atmosphere
3.1: water; barium hydroxide octahydrate / ethanol / Inert atmosphere; Reflux
3.2: 18 - 25 °C / pH 1 - 2
4.1: triethylamine; diphenyl phosphoryl azide / toluene / 4 h / 18 - 25 °C / Inert atmosphere; Reflux
4.2: Reflux
5.1: sodium hydroxide; water / methanol / 2 h / Inert atmosphere; Reflux
5.2: 18 - 25 °C / pH 1 - 2
6.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1 h / 18 - 25 °C / Inert atmosphere
7.1: ammonia / tetrahydrofuran / 0.5 h / 18 - 25 °C / Inert atmosphere
8.1: caesium carbonate / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 100 °C / Inert atmosphere
With
n-butyllithium; oxalyl dichloride; barium hydroxide octahydrate; diphenyl phosphoryl azide; ammonia; water; caesium carbonate; triethylamine; diisopropylamine; sodium hydroxide;
tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N,N-dimethyl-formamide;
In
tetrahydrofuran; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; ethanol; hexane; dichloromethane; toluene;
4.1: Curtius Rearrangement;