Diethyl Ether → 3-[2-(Cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amine

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Reaction Steps

To a solution of 4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (53 mg, 0.13 mmol) in N,N-dimethylformamide (4 mL) was added sodium azide (85 mg, 1.3 mmol). The resultant mixture was heated to 100° C. for 18 hours. The reaction mixture was cooled to room temperature and ether was added. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (2:1 to 1:1 hexanes:ethyl acetate) provided 3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-amine (30 mg, 60%) as an oil. 1H NMR (CDCl3) δ 7.97 (d, 1H), 7.77 (d, 1H), 7.60 (m, 2H), 7.22 (m, 1H), 7.10 (t, 2H), 6.26 (d, 1H), 6.14 (d, 1H), 5.26 (s, 2H), 5.09 (d, 1H), 4.29 (m, 1H), 2.06–1.99 (m, 2H), 1.75–1.45 (m, 6H); MS m/z 389 (M+1). This material was taken up in ether and treated with hydrochloric acid in ether to yield a yellow precipitate which was isolated by filtration as a hydrochloride salt.

Provenance & Evidence