Multi-step reaction with 12 steps
1.1: toluene-4-sulfonic acid / cyclohexane / 18 h / Molecular sieve; Reflux
2.1: acetonitrile / 72 h / 100 °C / Inert atmosphere
3.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 0.5 h / 80 °C
3.2: 2 h / -5 - -1 °C / Inert atmosphere
3.3: 0.25 h / 25 °C
4.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 18 h / 25 °C / 760.05 Torr
5.1: ammonium fluoride / methanol / 10 h / Inert atmosphere; Reflux
6.1: triphenylphosphine; carbon tetrabromide / acetonitrile / 24 h / Inert atmosphere
7.1: acetonitrile / 48 h / 100 °C
8.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 0.5 h / 80 °C
8.2: 2 h / -5 - -1 °C / Inert atmosphere
8.3: 0.25 h / 25 °C
9.1: acetic acid / water / 100 °C / Inert atmosphere
10.1: diethyl ether / 40 °C / Schlenk technique; Inert atmosphere
10.2: 25 °C / Inert atmosphere; Schlenk technique
11.1: diphenyldisulfane / cyclohexene / 25 °C / Inert atmosphere; Irradiation
12.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 - -40 °C / Schlenk technique; Inert atmosphere
12.2: 1 h / -40 - 25 °C / Schlenk technique; Inert atmosphere
With
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; ammonium fluoride; oxalyl dichloride; carbon tetrabromide; 5%-palladium/activated carbon; hydrogen; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triphenylphosphine; diphenyldisulfane;
In
methanol; diethyl ether; dichloromethane; cyclohexane; water; ethyl acetate; acetonitrile; cyclohexene;
DOI:10.1002/ejoc.202000145