Dichloromethane → 4-[4-(2-Methyl-6-[1,2,4]triazol-1-yl-pyridin-3-yloxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

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; 100 mg, 0.30 mmol), 2-methyl-6-[1,2,4]triazol-1-yl-pyridin-3-ol (Intermediate 7; 68 mg, 0.385 mmol), and potassium carbonate (53 mg, 0.385 mmol) in dimethylformamide (3 mL) was heated in the microwave oven at 160° C. for 10 min. Dichloromethane and water were added, and the aqueous layer was extracted three times with dichloromethane. The dichloromethane layers were combined, evaporated, and purified by preparative C18 HPLC, eluting with 10-100% acetonitrile/water. Samples containing the product were extracted three times with dichloromethane and the solvent was evaporated to give 4-[4-(2-methyl-6-[1,2,4]triazol-1-yl-pyridin-3-yloxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (96 mg, 68%) as a white powder. 1H NMR (300 MHz, CDCl3) δ 1.49 (s, 9H), 1.95-2.04 (m, 2H), 2.20-2.35 (m, 2H), 2.90-3.05 (m, 2H), 4.25-4.40 (m, 2H), 4.90-5.02 (m, 1H), 7.69 (d, 1H, J=8.5 Hz), 7.86 (d, 1H, J=8.8 Hz), 8.12 (s, 1H), 8.17 (s, 1H), 8.47 (s, 1H), 9.20 (s, 1H). Mass spectrum (ES) MH+=478. HRMS Calcd. for C23H28N9O3 (MH+): 478.2310. Found: 478.2307.

Provenance & Evidence