hydrogen; palladium on activated charcoal in ethanol

1: 6-hydroxyhexene With 9-bora-bicyclo[3.3.1]nonane in tetrahydrofuran T=25°C; 2: With water in tetrahydrofuran T=25°C; 1.5 h; 3: 5-bromo-pyrimidine With palladium diacetate; potassium phosphate; biphenyl-2-yl-di-tert-butyl-phosphane in tetrahydrofuran; water; toluene T=100°C; Suzuki cross-coupling; 19.5 h;

1: 25.3 g / Et3N, bis(triphenylphosphine)palladiumdichloride / CH2Cl2 / 3 h / Heating 2: 84 percent / H2 / Pd-C / ethanol View Scheme

1: 22.3 g / SOCl2 / CH2Cl2 / room temperature, 1 h -> reflux 1 h 2: 71 percent / KI / dimethylformamide / 1 h / Heating View Scheme

1: 22.3 g / SOCl2 / CH2Cl2 / room temperature, 1 h -> reflux 1 h 2: 71 percent / KI / dimethylformamide / 1 h / Heating 3: 90 percent / hydrazine hydrate / ethanol / 3 h / Heating View Scheme