Potassium Carbonate → 5-(2-Fluoro-3-pyridinyl)-2,4-bis(methyloxy)pyrimidine

Temperatur

90 °C

To a mixture of 5-bromo-2,4-bis(methyloxy)pyrimidine (Prep86, 3 g, 13.70 mmol), 2-fluoropyridine-3-boronic acid (1.930 g, 13.70 mmol) and Pd(PPh3)4 (0.791 g, 0.685 mmol), dry 1,4-Dioxane (45 ml) was added followed by potassium carbonate 1M solution (27.4 ml, 27.4 mmol). The mixture was degassed with Argon and then heated at 100° C. for 1 h (internal T˜90° C.). Then the mixture was cooled down to ambient, further 1 eq of boronic acid (1.930 g, 13.70 mmol) followed by 5 mol % of PdTetrakis (0.791 g, 0.685 mmol) were added and the mixture heated at 100° C. for two 2 h. The reaction mixture was cooled down to room temperature, taken up with water and AcOEt. The aqueous layer was back extracted with AcOEt. The combined organics were dried over Na2SO4 and evaporated to dryness. The crude material was purified by SiO2 flash chromatography eluting with Cy/EA 8/2 to get the title compound as white solid (3 g).

1. additionwas added
2. customThe mixture was degassed with Argon
3. temperatureThen the mixture was cooled down
4. additionwere added
5. temperaturethe mixture heated at 100° C. for two 2 h
6. temperatureThe reaction mixture was cooled down to room temperature
7. extractionThe aqueous layer was back extracted with AcOEt
8. dry with materialThe combined organics were dried over Na2SO4
9. customevaporated to dryness
10. customThe crude material was purified by SiO2 flash chromatography
11. washeluting with Cy/EA 8/2

ORD-Eintrag

ord-c4c1cbbe3d4c4342ab9166f0952850e1

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07727988B2