To a solution of methanol (25 mL) containing 0.40 g (1.58 mmol) of tert-butylmethyl (5-nitropyridin-2-yl) carbamate was added 0.4 g of 10% palladium/carbon catalyst. The reaction mixture was stirred under hydrogen atmosphere (40 g Hg pressure) for 4 hours. Upon completion of the reaction, the catalyst was removed by filtration through diatomaceous earth and the filtrate was concentrated to afford 0.36 g (97% yield) of 5-amino-2-(N-Boc-N-methylamino)pyridine, the product being a yellow oil. Its 1H NMR (DMSO-d6) data were as follows: δ 7.70 (dd, J = 2.9,0.5 Hz, 1H), 7.07 (d, J = 8.6 Hz, 1H), 6.93 (dd, J = 8.6,2.9 Hz, 1H), 3.12 (s, 3H), 1.39 (s, 9H).
