Imidazole → 2-Aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine

Participants

Reaction Steps

A solution of 6-aminomethypyridine-2-methanol (5 g, 36.2 mmol) in anhydrous DMF (25 mL) at 0° C. was treated with tert-butyldimethylsilyl chloride (5.728 g, 38 mmol) and imidazole (2.584 g, 38 mmol), stirred at room temperature for 20 h, poured into 1.5-M aqueous NaOH (100 mL) and extracted with EtOAc (3×20 mL). The combined organic phase was washed with water (4×10 mL), brine (2×20 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow oil; NMR δH (400 MHz, CDCl3) 0.82 (9H, s), 0.87 (6H, s), 1.81 (2H, s), 3.84 (2H, s), 4.73 (2H, s), 7.03 (1H, d, J 8.0 Hz), 7.28 (1H, d, J 7.5 Hz) and 7.57 (1H, t, J 8.0 Hz); M/Z 253 (M+H)+

Provenance & Evidence