2-Methoxyethylamine → 3-[2-(butylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-N-(2-methoxyethyl)pyrazolo[1,5-a]pyridin-7-amine

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A mixture of N-butyl-4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-pyrimidinamine (56 mg, 0.14 mmol) and 2-methoxyethylamine (5 mL) was heated to reflux for 24 hours, then cooled and concentrated. Flash column chromatography eluting with 3:1 hexanes:ethyl acetate afforded 3-[2-(butylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-N-(2-methoxyethyl)pyrazolo[1,5-α]pyridin-7-amine (57.1 mg, 93%) as a yellow foam. 1H NMR (CDCl3): δ 8.02 (d, 1H), 7.76 (d, 1H), 7.65 (m, 2H), 7.32 (t, 1H), 7.15 (t, 2H), 6.29 (m, 2H), 6.05 (d, 1H), 5.10 (broad, 1H), 3.72 (t, 2H), 3.57 (q, 2H), 3.47 (q, 2H), 3.43 (s, 3H), 1.69–1.44 (m, 4H), 0.98 (t, 3H); MS m/z 435 (M+1).

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