Multi-step reaction with 8 steps
1.1: sodium; ethanol / 20 °C
1.2: 75 percent / glacial acetic acid
2.1: 65 percent / methanol / 0.75 h / Heating
3.1: 60 percent / tert-butyl nitrite; CuCl2 / acetonitrile / 0.33 h / 65 °C
4.1: triethyl amine; hydrogen / 10 percent palladium on carbon / 2 h / 760 Torr
5.1: 60 percent / ammonia / 80 °C
6.1: 40 percent / dimethylsulfone / 1 h / 160 °C
7.1: aq. sodium hydroxide / 4 h / 20 °C
8.1: N-methylmorpholine; 6-chloro-2,4-dimethoxy-1,2,3-triazine / dimethylformamide / 1 h / 25 °C
8.2: 80 percent / N-methylmorpholine / dimethylformamide / 2 h / 20 °C
With
4-methyl-morpholine; sodium hydroxide; tert.-butylnitrite; ethanol; dimethylsulfone; 2-chloro-4,6-dimethoxy-4,3,5-triazine; ammonia; hydrogen; sodium; triethylamine; copper dichloride;
palladium on activated charcoal;
In
methanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/jhet.5570390613