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

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Reaction Steps

In a similar manner as described in Example 14, from N-butyl-4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-pyrimidinamine (53 mg, 0.13 mmol) and methylamine (5 mL, 40% aqueous) in a sealed tube was obtained 3-[2-(butylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-N-methylpyrazolo[1,5-α]pyridin-7-amine (40.5 mg, 77%) as a pale yellow solid. 1H NMR (CDCl3): δ 8.01 (d, 1H), 7.75 (d, 1H), 7.62 (m, 2H), 7.34 (t, 1H), 7.13 (t, 2H), 6.30 (d, 1H), 6.03–5.99 (m, 2H), 5.11 (broad, 1H), 3.46 (q, 2H), 3.10 (d, 3H), 1.69–1.42 (m, 4H), 0.97 (t, 3H); 19F NMR (CDCl3) δ −113.39; MS m/z 391 (M+1).

Provenance & Evidence