N-cyclopentyl-4-[2-isobutyl-7-(methylsulfinyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine → N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-isobutylpyrazolo[1,5-a]pyridin-7-amine

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A solution of N-cyclopentyl-4-[2-isobutyl-7-(methylsulfinyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine (110 mg, 0.28 mmol) in cyclopentylamine (5 mL) was heated at 130° C. for 72 h. The mixture was cooled to room temperature and concentrated in vacuo and the residue was purified by flash chromatography on silica gel (hexane-ethyl acetate) to give N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-isobutylpyrazolo[1,5-a]pyridin-7-amine (93 mg, 81%) as a White solid. 1H NMR (CDCl3) δ 8.20 (d, 1H), 7.50 (d, 1H), 7.21 (t, 1H), 6.74 (d, 1H), 5.97–5.92 (m, 2H), 5.09 (d, 1H), 4.38 (m, 1H), 3.96 (m, 1H), 3.01 (d, 2H), 2.27–2.04 (m, 5H), 1.81–1.50 (m, 12H), 0.97 (d, 6H); MS m/z 419 (M+1).

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