Multi-step reaction with 7 steps
1: 1.) n-BuLi / 1.) THF, hexane, RT, 15 min, 2.) THF, hexane, RT, 3 h
2: 85 percent / H2 / 10 percent Pd/C / ethanol / 24 h / 760 Torr
3: Et3N / CH2Cl2 / 0.25 h / 0 °C
4: 100 percent / BBr3 / CH2Cl2 / 2 h / -78 - 20 °C
5: 87 percent / N,N-diisopropylamine / CH2Cl2 / 48 h / Ambient temperature
6: 98 percent / NaI / acetone / 48 h / Heating
7: 1.) LDA, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, from -78 deg C to RT, overnight
With
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; hydrogen; boron tribromide; triethylamine; diisopropylamine; sodium iodide; lithium diisopropyl amide;
palladium on activated charcoal;
In
ethanol; dichloromethane; acetone;
DOI:10.1248/cpb.46.1770