Dichloromethane → HCID 57964916, 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), 2,6-dimethoxy-pyridin-3-ol (Aagile Labs Division of Tyger Scientific, Ewing, N.J., USA; 30 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 aqueous layer was extracted twice with dichloromethane. The dichloromethane layers were combined, evaporated, and purified by preparative C18 HPLC, eluting with 10-100% acetonitrile/water to give 4-[4-(2,6-dimethoxy-pyridin-3-yloxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (20 mg, 29%) as an off-white powder. 1H NMR (300 MHz, CDCl3) δ 1.49 (s, 9H), 1.96-2.04 (m, 2H), 2.18-2.30 (m, 2H), 2.90-3.05 (m, 2H), 3.90 (s, 3H), 3.95 (s, 3H), 4.25-4.38 (m, 2H), 4.90-5.00 (m, 1H), 6.37 (d, 1H, J=8.2 Hz), 7.41 (d, 1H, J=8.2 Hz), 8.03 (s, 1H), 8.50 (s, 1H). Mass spectrum MH+=457. HRMS Calcd. For C22H29N6O5 (MH+): 457.2194. Found: 457.2193.

Provenance & Evidence