Pyridine → N-(4-amino-6-propyl-pyridin-3-yl)-acetamide

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Reaction Steps

To a mixture of 6-propyl-pyridine-3,4-diamine hydrochloride (prepared from ethyl butyrylacetate as described in Example 28, steps 1-9) (187 mg, 1.00 mmol) in CH2Cl2 (4 mL) at 0° C. under N2 is added pyridine (0.24 mL, 3.00 mmol) followed by DMF (2 mL) (for solubility). Next, AC20 (0.104 mL, 1.1 mmol) is added. The reaction mixture is stirred for 3 h while slowly warming to rt. It is then poured into saturated aq NaHCO3 and extracted thrice with CH2Cl2. The combined extracts are dried over K2CO3 and concentrated to 114 mg of crude N-(4-amino-6-propyl-pyridin-3-yl)-acetamide, which was used without further purification. 1H NMR (CDCl3, 300 MHz) δ 8.73 (br, 1H), 8.00 (s, 1H), 8.43 (s, 1H), 4.63 (br, 2H), 2.54 (m, 2H), 2.13 (s, 3H), 1.63 (sextet, J=7.2 Hz, 2H), 0.89 (t, J=7.2 Hz, 3H) ppm. Electrospray MS: m/z 194 [M+1].

Provenance & Evidence