Reaktion #2018883

Reaktionsgleichung

4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

Intermediate 19

4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

5-hydroxy-2-methoxypyridine

potassium carbonate

Ethyl acetate

→

4-[4-(6-methoxy-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

Ausbeute 54.0%

Lösungsmittel

dimethylformamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe aqueous layer was extracted twice with ethyl acetate
2. 2
   Sonstigeevaporated
3. 3
   Sonstigepurified by preparative C18 HPLC
4. 4
   Wascheneluting with 10-100% acetonitrile/water
5. 5
   workup.ADDITIONSamples containing the product
6. 6
   Extraktionwere extracted twice with dichloromethane
7. 7
   Sonstigethe solvent was evaporated

Vorschrift

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), 5-hydroxy-2-methoxypyridine (Tyger Scientific, Ewing, N.J., USA; 24 mg, 0.19 mmol), and potassium carbonate (27 mg, 0.19 mmol) in dimethylformamide (2 mL) was heated in the microwave oven at 160° C. for 10 min. Ethyl acetate and water were added, and the aqueous layer was extracted twice with ethyl acetate. The ethyl acetate layers were combined, evaporated, and purified by preparative C18 HPLC, eluting with 10-100% acetonitrile/water. Samples containing the product were extracted twice with dichloromethane and the solvent was evaporated to give 4-[4-(6-methoxy-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (34 mg, 54%) as a white powder. Mass spectrum (ES) MH+=427. HRMS Calcd. for C21H27N6O4 (MH+): 427.2089. Found: 427.2088.

Quelle