Reaktion #58365

Reaktionsgleichung

sodium carbonate

4-chloro-8-(2,6-difluorophenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

4-fluorobenzeneboronic acid

→

title compound

Ausbeute 63.0%

8-(2,6-Difluorophenyl)-4-(2-methylphenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Ausbeute 63.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was irradiated with microwave at about 150° C. for about 20 min
2. 2
   Filtrationfiltered
3. 3
   Sonstigethe filtrate evaporated
4. 4
   workup.DISSOLUTIONThe crude product was redissolved in ethyl acetate (10 mL)
5. 5
   SonstigeThe layers were separated
6. 6
   Trocknenthe organic layer was dried over magnesium sulphate
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe crude product was purified by flash chromatography on silica gel with cyclohexane
10. 10
    workup.ADDITIONcontaining ethyl acetate (0 to 50%)

Vorschrift

THF (10 mL) and 2M sodium carbonate (2 mL) were added to a mixture of 4-chloro-8-(2,6-difluorophenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (0.34 g, 1.0 mmol, solid-supported tetrakis(triphenylphosphine)palladium(0) (0.39 g, 0.1 mmol) and 4-fluorobenzeneboronic acid (0.21 g, 1.5 mmol). The mixture was irradiated with microwave at about 150° C. for about 20 min, then filtered and the filtrate evaporated. The crude product was redissolved in ethyl acetate (10 mL) and water (10 mL). The layers were separated and the organic layer was dried over magnesium sulphate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel with cyclohexane containing ethyl acetate (0 to 50%) to give the title compound (0.25 g, 63%). LC-MS m/z 396 (M+H)+, 3.55 min (ret time).

Quelle