Allyl Alcohol → 6-Chloro-2-phenylmethoxy-4-(2-propenyloxy)pyrimidine

HRID 1449438노트

반응식

HRID 1449438 반응식
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1.[CH2:17]([OH:20])[CH:18]=[CH2:19].[H-].[Na+]>CN(C)C=O>[Cl:8][C:6]1[N:5]=[C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=[C:2]([O:20][CH2:17][CH:18]=[CH2:19])[CH:7]=1

참가 물질

5

반응물 3

HCID 7858Allyl AlcoholHCID 24758Sodium hydrideHCID 196938984,6-Dichloro-2-(phenylmethoxy)pyrimidine

생성물 1

HCID 196938826-Chloro-2-phenylmethoxy-4-(2-propenyloxy)pyrimidine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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).

후처리

  1. additionwas added
  2. customto form a solution
  3. washhad been washed with hexane
  4. additionwas added
  5. additionthe reaction solution was poured into iced water
  6. extractionextracted with toluene (40 ml)
  7. washThe organic phase was washed with saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off
  10. customto afford an oily product, which
  11. customwas then purified on silica gel column chromatography (Wakogel C300, 300 ml, hexane/ethyl acetate=25/1000(v/v))
  12. customto obtain the compound (I-343)

출처 및 근거

ORD 기록
ord-3266352ec5474fa5bf2757fac2b8a492
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05599770

반응 노트

불러오는 중…