Reaktion #1536620

Reaktionsgleichung

4,6-Dichloro-2-(phenylmethoxy)pyrimidine

allyl alcohol

sodium hydride

→

6-chloro-2-phenylmethoxy-4-(2-propenyloxy)pyrimidine

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigeto form a solution
3. 3
   Waschenhad been washed with hexane
4. 4
   workup.ADDITIONwas added
5. 5
   workup.ADDITIONthe reaction solution was poured into iced water
6. 6
   Extraktionextracted with toluene (40 ml)
7. 7
   WaschenThe organic phase was washed with saturated aqueous sodium chloride
8. 8
   Trocknendried over anhydrous sodium sulfate
9. 9
   workup.DISTILLATIONthe solvent was distilled off
10. 10
    Sonstigeto afford an oily product, which
11. 11
    Sonstigewas then purified on silica gel column chromatography (Wakogel C300, 300 ml, hexane/ethyl acetate=25/1000(v/v))
12. 12
    Sonstigeto obtain the compound (I-343)

Vorschrift

4,6-Dichloro-2-(phenylmethoxy)pyrimidine (Compound I-173) (1.5 g, 5.9 mmol) and allyl alcohol (0.342 g, 5.9×1.0 mmol) were introduced into a 50 ml eggplant type flask, to which dimethylformamide (20 ml) was added to form a solution. While cooling with ice, 60% sodium hydride (0.247 g, 5.9×1.05 mmol) which had been washed with hexane was added. After stirred for one night at room temperature, the reaction solution was poured into iced water and extracted with toluene (40 ml). The organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and thereafter, the solvent was distilled off to afford an oily product, which was then purified on silica gel column chromatography (Wakogel C300, 300 ml, hexane/ethyl acetate=25/1000(v/v)) to obtain the compound (I-343).

Quelle