Reaktion #1112015

Reaktionsgleichung

4,6-Dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine

product

4,6-Dichloro-2[(2,3-difluorobenzyl)thio]pyrimidine

2-phenyl-1,3-dioxan-5-ol

sodium hydride

→

sub-title compound

4-chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-[(2-phenyl-1,3-dioxan-5-yl)oxy]-pyrimidine

Lösungsmittel

water

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturto reflux for 25 minutes
3. 3
   workup.ADDITIONwas added
4. 4
   Temperaturthe reaction was heated
5. 5
   Temperaturto reflux for a further 90 minutes
6. 6
   Temperaturto cool
7. 7
   Extraktionextracted with ethyl acetate (×3)
8. 8
   TrocknenThe combined organic layers were dried with magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated
11. 11
    SonstigeThe residue was purified by column chromatography on silica using a 95:5
12. 12
    workup.ADDITIONto 90:10 mixture of iso-hexane and ethyl acetate as eluent

Vorschrift

To a solution of 2-phenyl-1,3-dioxan-5-ol (484 mg) in anhydrous tetrahydrofuran (10 ml) at 0° C. was added 60% sodium hydride (110 mg) and the mixture was heated to reflux for 25 minutes. On allowing to cool to ambient temperature 4,6-Dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of step (ii) (75 mg) was added and the reaction was heated to reflux for a further 90 minutes. The reaction mixture was allowed to cool, diluted with water and extracted with ethyl acetate (×3). The combined organic layers were dried with magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography on silica using a 95:5 to 90:10 mixture of iso-hexane and ethyl acetate as eluent to give the sub-title compound as a white solid. Yield: 350 mg

Quelle