Tetrahydrofuran → 2-(2,2-Diethoxyethoxy)-5-fluoropyrimidine

HRID 81629

反応式

HRID 81629 の反応式
O1CCCC1.[CH2:6]([O:8][CH:9]([O:12][CH2:13][CH3:14])[CH2:10][OH:11])[CH3:7].CN(C)C(=O)C.[Cl:21][C:22]1[N:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=1>O>[CH2:6]([O:8][CH:9]([O:12][CH2:13][CH3:14])[CH2:10][O:11][C:22]1[N:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=1)[CH3:7].[Cl:21][C:22]1[N:27]=[CH:26][C:25]([O:11][CH2:10][CH:9]([O:12][CH2:13][CH3:14])[O:8][CH2:6][CH3:7])=[CH:24][N:23]=1

参加物

7

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 121292,2-DiethoxyethanolHCID 31374DimethylacetamideHCID 5834662-Chloro-5-fluoropyrimidine

生成物 2

HCID 684276832-(2,2-Diethoxyethoxy)-5-fluoropyrimidine収率 67%HCID 866458972-Chloro-5-(2,2-diethoxyethoxy)pyrimidine収率 21%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

With cooling with ice, a tetrahydrofuran solution (2 ml) of 2,2-diethoxyethanol (668 mg, 4.98 mmol) was added to a mixed tetrahydrofuran (4 ml)/N,N-dimethylacetamide (2 ml) solution of 2-chloro-5-fluoropyrimidine (600 mg, 4.53 mmol), and stirred under a nitrogen atmosphere for 1 hour. Water was added to the reaction solution, and extracted with ethyl acetate. Next, the organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Moritex, acetone:hexane=1:25) to obtain 2-(2,2-diethoxyethoxy)-5-fluoropyrimidine (699 mg, yield: 67%) as a colorless oil, and 2-chloro-5-(2,2-diethoxyethoxy)pyrimidine (233 mg, 21%) as a colorless solid.

後処理

  1. temperatureWith cooling with ice
  2. extractionextracted with ethyl acetate
  3. washNext, the organic layer was washed with saturated saline water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (Moritex, acetone:hexane=1:25)

出典と根拠

ORDレコード
ord-e27b373c1e6a4e388b8ecb2abf664fe7
出典データセット
uspto-grants-2014_09
特許番号
US08846700B2

関連ノート

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