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

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Reaction Steps

To a solution of N-allyl-3-[2-(butylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-amine (80 mg, 0.19 mmol) in ethanol (5 mL) was added palladium on carbon (10%, 8 mg). The mixture was stirred overnight at room temperature under a balloon filled with hydrogen. The reaction was filtered through a pad of Celite and concentrated to give 3-[2-(butylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-N-propylpyrazolo[1,5-α]pyridin-7-amine (79 mg, 99%) as a gold foam. 1H NMR (CDCl3): δ 8.03 (d, 1H), 7.74 (d, 1H), 7.69 (m, 2H), 7.33 (t, 1H), 7.15 (t, 2H), 6.30 (d, 1H), 6.08–6.01 (m, 2H), 5.08 (broad, 1H), 3.47 (q, 2H), 3.37 (q, 2H), 1.87–1.41 (m, 6H), 1.08 (t, 3H), 0.99 (t, 3H); 19F NMR (CDCl3) δ −113.44; MS m/z 419 (M+1).

Provenance & Evidence