4-(N,N-dimethlyamino)pyridine; triethylamine in pyridine

1: 90 percent / imidazole / dimethylformamide / 12 h / 20 °C 2: BH3*THF / tetrahydrofuran / 7 h / 0 °C 3: 21.5 g / H2O2; NaOH / H2O / 0 - 20 °C 4: 95 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 15 h / 20 °C 5: 75 percent / PtO2; H2 / ethanol / 2 h / 20 °C 6: 92 percent / pyridine / CH2Cl2 / 3 h / Heating 7: 96 percent / tetra-n-butylammmonium fluoride / tetrahydrofuran / 6 h / 20 °C 8: 66 percent / o-iodoxybenzoic acid / 14 h / 20 °C 9: 78 percent / HCl / methanol / 1 h / 20 °C 10: 77 percent / diethyl azodicarboxylate; PPh3 / tetrahydrofuran / 3 h / 20 °C View Scheme