Chlorine → 1-(2,4-Dichloropyrimidin-5-yl)ethan-1-one

HRID 750485ノート

反応式

HRID 750485 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([OH:11])[CH3:10])=[CH:4][N:3]=1.CC1(C)N([O])C(C)(C)CCC1.C(=O)(O)[O-].[Na+].ClCl>C(Cl)Cl.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9](=[O:11])[CH3:10])=[CH:4][N:3]=1

参加物

9

反応物 4

HCID 24526ChlorineHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 151416481-(2,4-Dichloropyrimidin-5-yl)ethan-1-ol

生成物 1

HCID 212747081-(2,4-Dichloropyrimidin-5-yl)ethan-1-one

試薬・触媒・溶媒 4

HCID 70681Tetrabutylammonium Chloride触媒HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred suspension of 1-(2,4-dichloro-pyrimidin-5-yl)-ethanol (Example 20, 1.00 g, 5.2 mmol) in a mixture of methylene chloride (30 mL), THF (8 mL) and water (2 mL), tetrabutylammonium chloride (Aldrich, 50 mg, 0.15 mmol), TEMPO (Aldrich, 9 mg, 0.05 mmol) and sodium bicarbonate (208 mg, 2.48 mmol) were added and the mixture was cooled to 0° C. To the stirred mixture, colorex (Aldrich; active Cl2, 10-13%; 3.75 mL) was added and the mixture was stirred for 2 hours at 0° C. Water (10 mL) was added and the organic layer was separated and dried over sodium sulfate. Removal of solvent gave an oil which was purified by silica gel chromatography (1% MeOH/CH2Cl2) to yield a colorless oil. 232 mg, 23%. MS (M+H)+, 191.

後処理

  1. additionwere added
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customRemoval of solvent
  5. customgave an oil which
  6. customwas purified by silica gel chromatography (1% MeOH/CH2Cl2)
  7. customto yield a colorless oil

出典と根拠

ORDレコード
ord-08afe15dbd4d464195433ac037f25b92
出典データセット
uspto-grants-2008_07
特許番号
US07405220B2

反応ノート

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