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

HRID 1449438ノート

反応式

HRID 1449438 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3266352ec5474fa5bf2757fac2b8a492
出典データセット
uspto-grants-1997_02
特許番号
US05599770

反応ノート

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