Reaktion #1132857

Reaktionsgleichung

2-Mercapto-1-methyl-2′-phenyl-1H-[4,4′]bipyrimidinyl-6-one

phosphorus oxychloride

water

sodium bicarbonate

→

2-chloro-1-methyl-2′-phenyl-1H-[4,4′]bipyrimidinyl-6-one

Ausbeute 75.0%

Lösungsmittel

1,2-dichloroethane

N-methylpyrrolidone

N-methylpyrrolidone

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe solution was poured
2. 2
   workup.ADDITIONwas added to the solution
3. 3
   workup.STIRRINGthe mixture was stirred until no gas
4. 4
   SonstigeThe resulting solution was partitioned between water and dichloromethane
5. 5
   Waschenthe organic layer was washed with water and brine
6. 6
   SonstigeThe solvent was removed under reduced pressure
7. 7
   Sonstigethe residue was purified with silica gel column chromatography (eluent; hexane/ethyl acetate=2/1 to 1/1)

Vorschrift

2-Mercapto-1-methyl-2′-phenyl-1H-[4,4′]bipyrimidinyl-6-one (2.76 g, 9.33 mmol) in 1,2-dichloroethane (20 ml) and N-methylpyrrolidone (2 ml) was added to a solution of phosphorus oxychloride (3.83 g, 25.0 mmol) and N-methylpyrrolidone (5.22 g, 52.7 mmol) at 50° C. and the mixture was stirred for 20 minutes. The solution was poured into warm water, and sodium bicarbonate (10.2 g, 121 mmol) was added to the solution and the mixture was stirred until no gas was generated. The resulting solution was partitioned between water and dichloromethane, and the organic layer was washed with water and brine and passed through Celite. The solvent was removed under reduced pressure, and the residue was purified with silica gel column chromatography (eluent; hexane/ethyl acetate=2/1 to 1/1) to afford 2-chloro-1-methyl-2′-phenyl-1H-[4,4′]bipyrimidinyl-6-one (2.08 g, 75%).

Quelle