반응 #1536620

반응 방정식

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

allyl alcohol

sodium hydride

→

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

용매

dimethylformamide

반응 조건

후처리

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

실험 절차

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).

출처