Diethyl Ether → 4-[7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine

関与物質

反応手順

To a solution of 1-[7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one (4.04 g, 13.0 mmol) in N,N-dimethylformamide (100 mL) was added cyclopentyl guanidine hydrochloride (6.36 g, 39 mmol), followed by solid potassium carbonate (5.39 g, 39 mmol). The resultant solution was heated to reflux for 6 hours. Upon cooling to room temperature, ether was added followed by water. The organics were washed with brine, and the aqueous extracted with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography (3:10 ethyl acetate:hexanes) to give 4-[7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (2.39 g, 43%) as a yellow foam. 1H NMR (CDCl3) δ 8.47 (d, 1H), 7.99 (d, 1H), 7.48 (s, 1H), 7.39 (d, 1H), 7.33–7.24 (m, 3H), 7.05 (d, 1H), 6.33 (d, 1H), 5.38 (broad s, 1H), 4.36 (m, 1H), 2.40 (s, 3H), 2.10 (m, 2H), 1.78 (m, 2H), 1.67 (m, 2H), 1.58 (m, 2H); MS m/z 404 (M+1).

情報源と証拠