Dichloromethane → HCID 53257684, 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; 50 mg, 0.15 mmol), 4-methoxy-phenol (Aldrich Chemical Company, Inc., Milwaukee, Wis., USA 24 mg, 0.19 mmol), and potassium carbonate (27 mg, 0.2 mmol) in dimethylformamide (2 mL) was heated in the microwave oven at 160° C. for 10 min. Dichloromethane and water were added, and the dichloromethane layer was washed twice with water. The dichloromethane layer was evaporated, and purified by preparative C18 HPLC, eluting with 25-100% acetonitrile/water to give 4-[4-(4-methoxy-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (19 mg, 28%) as an off-white powder. 1H NMR (300 MHz, CDCl3) δ 1.49 (s, 9H), 1.95-2.02 (m, 2H), 2.16-2.30 (m, 2H), 2.90-3.04 (m, 2H), 3.85 (s, 3H), 4.22-4.37 (m, 2H), 4.88-4.99 (m, 1H), 6.98 (d, 1H, J=8.7 Hz), 7.16 (d, 1H, J=8.9 Hz), 7.77 (s, 1H), 8.54 (s, 1H). Mass spectrum MH+=426. HRMS Calcd. For C22H28N5O4 (MH+): 426.2136. Found: 426.2134.

Provenance & Evidence