2,4-Dichlorophenol → HCID 57965056, 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; 42 mg, 0.12 mmol), anhydrous potassium carbonate (22 mg, 0.16 mmol) and 2,4-dichlorophenol (26 mg, 0.16 mmol) in N-methylpyrrolidinone (0.5 mL) was heated to 100° C. in a sealed scintillation vial. After 18 hr, the mixture was allowed to cool to room temperature and the reaction mixture purified by reverse phase HPLC to give 4-[4-(2,4-dichloro-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (8 mg, 14%) as a white powder. 1H NMR (300 MHz, CDCl3) δ 1.49 (s, 9H), 1.97-2.05 (m, 2H), 2.18-2.33 (m, 2H), 2.90-3.04 (m, 2H), 4.24-4.40 (m, 2H), 4.90-5.02 (m, 1H), 7.23-7.25 (m, 1H), 7.36 (dd, 1H, J=8.6, 2.6 Hz), 7.64 (d, 1H, J=2.1 Hz), 8.12 (s, 1H), 8.49 (s, 1H). Mass spectrum MH+=464.

Provenance & Evidence