Methyl iodide → N-butyl-2-(4-fluorophenyl)-3-[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-amine

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Reaction Steps

A mixture of 4-[7-(butylamino)-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-pyrimidinethiolate (2.87 g, 6.9 mmol) in 50 mL water was treated with iodomethane (0.86 mL, 13.8 mmol) and sodium hydroxide (4.1 mL, 5 N aqueous solution) and allowed to stir at room temperature for 4 hours. The mixture was diluted with additional water and extracted with dichloromethane. The organic layers were washed with brine, dried over magnesium sulfate and concentrated. Flash column chromatography eluting with 9:1 hexanes-ethyl acetate afforded N-butyl-2-(4-fluorophenyl)-3-[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-α]pyridin-7-amine (1.64 g, 56%) as a yellow foam. 1H NMR (CDCl3): δ 8.15 (d, 1H), 7.73 (d, 1H), 7.56 (m, 2H), 7.33 (t, 1H), 7.13 (t, 2H), 6.62 (d, 1H), 6.02 (m, 2H), 3.35 (q, 2H), 2.55 (s, 3H), 1.76–1.41 (m, 4H), 0.95 (t, 3H); 19F NMR (CDCl3): δ −112.75; MS m/z 408 (M+1).

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