Heptanoyl chloride → 2-Decyl-5-(3-fluoro-4-heptanoyloxyphenyl)pyrimidine

HRID 274824

反応式

HRID 274824 の反応式
[CH2:1]([C:11]1[N:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([F:24])[CH:18]=2)=[CH:13][N:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:25](Cl)(=[O:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].CC(C)=O.CO>N1C=CC=CC=1>[CH2:1]([C:11]1[N:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:25](=[O:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[C:19]([F:24])[CH:18]=2)=[CH:13][N:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

参加物

5

反応物 3

HCID 17313Heptanoyl chlorideHCID 150271672-Decyl-5-(3-fluoro-4-hydroxyphenyl)pyrimidineHCID 21894497Aceton-methanol

生成物 1

HCID 150271682-Decyl-5-(3-fluoro-4-heptanoyloxyphenyl)pyrimidine収率 61.6%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

0.80 g (2.42 mmol) of 2-decyl-5-(3-fluoro-4-hydroxyphenyl) pyrimidine was dissolved in 10 ml of pyridine before 0.62 ml (4.00 mmol) of heptanoylchloride was added dropwise thereto while being cooled with ice and stirred. Then, the solution was cooled with ice and stirred for 15 minutes before it was heated and stirred for another 20 minutes in a water bath having a temperature maintained at 45° to 56° C. After the reaction had been completed, the solution was injected into 150 ml of ice water so as to filter and wash with water the deposited crystal. The thus obtained crystal was dissolved in toluene and the resultant toluene layer was washed with water and dried with dried mirabilite. The solvent was removed by lowering the pressure and distillation. The residue was purified by the silica gel column chromatography method which uses toluene as the eluate before it was recrystallized twice by an acetone-methanol mixed solvent so that 0.66 g (yield 61.6%) of 2-decyl-5-(3-fluoro-4-heptanoyloxyphenyl) pyrimidine was obtained.

後処理

  1. additionwas added dropwise
  2. temperaturewhile being cooled with ice
  3. temperatureThen, the solution was cooled with ice
  4. stirringstirred for 15 minutes before it
  5. temperaturewas heated
  6. stirringstirred for another 20 minutes in a water bath
  7. temperaturemaintained at 45° to 56° C
  8. filtrationto filter
  9. washwash with water the deposited crystal
  10. dissolutionThe thus obtained crystal was dissolved in toluene
  11. washthe resultant toluene layer was washed with water
  12. dry with materialdried with dried mirabilite
  13. customThe solvent was removed
  14. distillationthe pressure and distillation
  15. customThe residue was purified by the silica gel column chromatography method which

出典と根拠

ORDレコード
ord-6dd6ca04b52449b286ad6a2771e7457a
出典データセット
uspto-grants-1995_02
特許番号
US05391318

関連ノート

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