Allylamine → N-allyl-3-[2-(butylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amine

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Reaction Steps

A solution of N-butyl-4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-pyrimidinamine (0.15 g, 0.38 mmol) in allylamine (5 mL, 67 mmol) was heated at 85° C. in a sealed tube for 88 hours. After cooling and concentrating the reaction mixture, flash chromatography (4:1 hexanes-ethyl acetate) afforded N-allyl-3-[2-(butylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-amine (0.14 g, 88%) as a pale yellow foam. 1H NMR (CDCl3): δ 7.89 (broad, 1H), 7.78 (d, 1H), 7.62 (m, 2H), 7.36 (t, 1H), 7.16 (t, 2H), 6.31–6.26 (m, 2H), 6.09–5.92 (m, 2H), 5.39–5.24 (m, 2H), 4.06 (t, 2H), 3.50 (q, 2H), 1.72–1.41 (m, 4H), 0.98 (t, 3H); 19F NMR (CDCl3) δ −113.16; MS m/z 417 (M+1); Anal. Calcd for C24H25FN6: C, 69.21; H, 6.05; N, 20.18. Found: C, 69.27; H, 6.07; N, 20.03.

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