Reaktion #164706

Reaktionsgleichung

dichloromethane

4,6-Dichloro-pyrimidine

(2-methoxy-phenyl)-boronic acid

NaHCO3

→

2-chloro-4-(2-methoxy-phenyl)-pyrimidine

Ausbeute 73.0%

Lösungsmittel

dimethoxyethane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux for 7 his (TLC control)
2. 2
   Sonstigethe solvents removed under reduced pressure
3. 3
   SonstigeThe obtained crude solid
4. 4
   Waschenwashed with water (1×100 mL)
5. 5
   Sonstigethe organic layer was separated
6. 6
   Trocknendried over K2CO3
7. 7
   Filtrationfiltered
8. 8
   Sonstigethe solvent removed under reduced pressure
9. 9
   SonstigeThe obtained solid was further purified by flash-chromatography (eluent dichloromethane)
10. 10
    Sonstigeto afford a crude product that
11. 11
    Sonstigewas crystallized from hexane

Vorschrift

4,6-Dichloro-pyrimidine (6 g, 0.04 mol) (Ranganathan, Subramania et al., Proceedings—Indian Academy of Sciences, Chemical Sciences (1994), 106(5), 1051-70. Maggieli, C. et al., Farmaco, Edizione Scientifica (1988), 43(3), 277-91. Gershon, Herman et al., Journal of Med. Chem. (1963), 6, 87-9) and (2-methoxy-phenyl)-boronic acid (4.37 g, 0.029 mol) were dissolved in dimethoxyethane (120 mL) and water (18 mL). To this solution were added NaHCO3 (6.72 g, 0.08 mol), PdCl2(PPh3)2 (0.84 g) and allowed to reflux for 7 his (TLC control). Then the mixture was cooled down to room temperature and the solvents removed under reduced pressure. The obtained crude solid was dissolved in dichloromethane (100 mL), washed with water (1×100 mL), the organic layer was separated, dried over K2CO3, filtered and the solvent removed under reduced pressure. The obtained solid was further purified by flash-chromatography (eluent dichloromethane) to afford a crude product that was crystallized from hexane to yield 2-chloro-4-(2-methoxy-phenyl)-pyrimidine (4.7 g, 73%).

Quelle