3-Pyridinol,6-chloro-2-methyl-(9CI) → HCID 57964983, compound

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4-[4-(6-Chloro-2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester was prepared in 19% yield as a white powder using Method A described for the preparation of Example 92 by the reaction of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 50 mg, 0.15 mmol) with 6-chloro-2-methyl-pyridin-3-ol (Intermediate 3; 28 mg, 0.19 mmol). 1H NMR (300 MHz, CDCl3) δ 1.50 (s, 9H), 1.96-2.06 (m, 2H), 2.20-2.35 (m, 2H), 2.42 (s, 3H), 2.92-3.05 (m, 2H), 4.26-4.38 (m, 2H), 4.90-5.02 (m, 1H), 7.27-7.30 (m, 1H), 7.48 (d, 1H, J=8.4 Hz), 8.15 (s, 1H), 8.47 (s, 1H). Mass spectrum (ES) MH+=445. HRMS Calcd. for C21H26ClN6O3 (MH+): 445.1750. Found: 445.1750.

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