Reaktion #40990

Reaktionsgleichung

5-bromo-2,4-bis(methyloxy)pyrimidine

2-fluoropyridine-3-boronic acid

boronic acid

potassium carbonate

→

title compound

Ausbeute 93.1%

5-(2-fluoro-3-pyridinyl)-2,4-bis(methyloxy)pyrimidine

Ausbeute 93.1%

Lösungsmittel

AcOEt

water

1,4-Dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   SonstigeThe mixture was degassed with Argon
3. 3
   TemperaturThen the mixture was cooled down
4. 4
   workup.ADDITIONwere added
5. 5
   Temperaturthe mixture heated at 100° C. for two 2 h
6. 6
   TemperaturThe reaction mixture was cooled down to room temperature
7. 7
   ExtraktionThe aqueous layer was back extracted with AcOEt
8. 8
   TrocknenThe combined organics were dried over Na2SO4
9. 9
   Sonstigeevaporated to dryness
10. 10
    SonstigeThe crude material was purified by SiO2 flash chromatography
11. 11
    Wascheneluting with Cy/EA 8/2

Vorschrift

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).

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