hydrogenchloride in tetrahydrofuran T=50°C; 3 h;

1.1: 92 percent / NaH / dimethylformamide / 3 h / 20 °C 2.1: MeLi; diisopropylamine / tetrahydrofuran / 3 h / 0 °C 2.2: 62 percent / tetrahydrofuran / 2 h / -40 °C 3.1: 95 percent / aq. HCl / tetrahydrofuran / 3 h / 50 °C View Scheme

1.1: MeLi; diisopropylamine / tetrahydrofuran / 3 h / 0 °C 1.2: 62 percent / tetrahydrofuran / 2 h / -40 °C 2.1: 95 percent / aq. HCl / tetrahydrofuran / 3 h / 50 °C View Scheme

1: 5-hydroxy-2-methoxy-pyridine-4-carbaldehyde With potassium carbonate in N,N-dimethyl-formamide T=50°C; 0.166667 h; 2: methyl iodide in N,N-dimethyl-formamide T=50°C; 3 h;