Reaktion #47944

Reaktionsgleichung

acetic acid

Benzyl alcohol

sodium hydride

4-chloro-2-(methylthio)pyrimidine

→

title compound

2-(methylthio)-4-[(phenylmethyl)oxy]pyrimidine

Lösungsmittel

dioxane

water

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at this temperature for 5 hours
2. 2
   TemperaturAfter cooling at room temperature the mixture
3. 3
   Extraktionextracted with dichloromethane
4. 4
   TrocknenThe organic phases were dried over anhydrous Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe crude product was purified by a silica SPE cartridge (70 g)
8. 8
   Wascheneluting with ciclohexane/ethyl acetate from 95/5 to 9/1

Vorschrift

Benzyl alcohol (1.3 mL) was added dropwise to a suspension of sodium hydride (60% in mineral oil, 0.74 g) in 12.4 mL of dry dioxane, and the mixture was stirred at 100° C. for 30 min. A solution of 4-chloro-2-(methylthio)pyrimidine (2.0 g) in dry dioxane (8.2 mL) was added dropwise at 50° C. and the mixture was stirred at this temperature for 5 hours. After cooling at room temperature the mixture was acidified with glacial acetic acid, treated with water and extracted with dichloromethane. The organic phases were dried over anhydrous Na2SO4 filtered and concentrated under reduced pressure. The crude product was purified by a silica SPE cartridge (70 g) eluting with ciclohexane/ethyl acetate from 95/5 to 9/1 to give the title compound as a white solid (1.22 g).

Quelle