Multi-step reaction with 13 steps
2: 93 percent / 7-methyl-1,5,7-triazabicyclo<4.4.0>dec-5-ene, molecular sieves (4 angstroem) / toluene / 3 h / Heating
3: 98 percent / 2.5 M NaOMe / methanol / 20 h
4: 93 percent / 2,6-dimethylpyridine / dimethylformamide / 24 h / Ambient temperature
5: 88 percent / H2 / 10percent Pd-C / methanol / 192 h
6: 85 percent / tetrahydrofuran / a.) 1h, 0 deg C b.) 3h, r. t.
7: 88 percent / Et3N / CH2Cl2 / 0.08 h / -20 °C
8: 68 percent / KNO2 / dimethylformamide / 1 h / 100 °C
9: Et3N / CH2Cl2 / 0.08 h / -20 °C
10: 75 percent / dimethylformamide / 12 h / Ambient temperature
11: 1.) O3/O2 2.) NaHCO3, PPh3 / 1.) CH2Cl2, -78 deg C, 5 min 2.) CH2CH2, 1h, r. t.
12: 80 percent / HCOONH4 / 10percent Pd-C / methanol / 3 h / Ambient temperature
13: 87 percent / aq. CF3COOH / 1 h / Ambient temperature
With
2,6-dimethylpyridine; potassium nitrite; 4 A molecular sieve; hydrogen; oxygen; ammonium formate; sodium methylate; sodium hydrogencarbonate; ozone; triethylamine; triphenylphosphine; 1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.19910740214