Multi-step reaction with 7 steps
1: H2, 5 N HCl / Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature
2: HOBt*H2O, i-Pr2NEt, EDC / tetrahydrofuran; dimethylformamide / 24 h / 0 - 20 °C
4: 98 percent / NaI / acetone / 6 h / Heating
5: 61 percent / DMPU, SmI2 / tetrahydrofuran / 0 deg C, 10 min; room temperature, 3 h
6: thioanisol, TFA / CH2Cl2 / 1.5 h / 0 °C
7: NaHCO3, DPPA / dimethylformamide / 72 h / 0 °C
With
hydrogenchloride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; samarium diiodide; methyl-phenyl-thioether; diphenyl-phosphinic acid; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium iodide;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo960956l