Potassium Carbonate → HCID 44622155, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 3.00 g, 8.9 mmol), 3-hydroxy-2-methylpyridine (Aldrich Chemical Company, Inc., Milwaukee, Wis., USA 1.26 g, 12 mmol), and potassium carbonate (1.59 g, 11.5 mmol) in dimethylformamide (30 mL) was heated at 100° C. overnight. The solvent was evaporated under high vacuum. Water (50 mL) and dichloromethane (50 mL) were added. The layers were separated and the organic layer was washed twice with water and then evaporated to dryness to give 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (3.24 g, 89%). A sample of this material (500 mg) was purified by silica gel column chromatography, eluting with 0-75% ethyl acetate/hexanes, to give 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (381 mg, 10%) as a white powder. 1H NMR (300 MHz, CDCl3) δ 1.49 (s, 9H), 1.97-2.06 (m, 2H), 2.20-2.34 (m, 2H), 2.47 (s, 3H), 2.91-3.05 (m, 2H), 4.26-4.39 (m, 2H), 4.91-5.03 (m, 1H), 7.27-7.29 (m, 1H), 7.50-7.55 (m, 1H), 8.07 (s, 1H), 8.48-8.51 (m, 2H). Mass spectrum MH+=411. HRMS Calcd. For C21H27N6O3 (MH+): 411.2139. Found: 411.2137.

Provenance & Evidence