N-Iodosuccinimide → 2-Butoxy-3-iodo-6-methylpyridin-4-amine

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Reaction Steps

2-butoxy-6-methylpyridin-4-amine (31 g, 0.17 mol) was dissolved in THF (500 mL), and then N-iodosuccinimide (32 g, 0.14 mol) was added portionwise at −78° C. The reaction mixture was stirred at the same temperature for 2 min. The reaction was quenched by addition of water, and the resulting mixture was extracted with ethyl acetate (2×600 mL). The combined organic layers were washed with brine (500 mL), dried over sodium sulfate, and concentrated. The crude was purified by silica gel column chromatography (petroleum ether) to afford 2-butoxy-3-iodo-6-methylpyridin-4-amine. 1H NMR (400 MHz, CDCl3): δ 6.10 (s, 1H), 4.49 (m, 2H), 4.29 (t, J=6.4 Hz, 2H), 2.284 (s, 1H), 1.75 (m, 2H), 1.50 (m, 2H), 0.98 (t, J=7.6 Hz, 3H). LRMS calc'd for (C10H151N2O) [M+H]+, 307; found 307.

Provenance & Evidence