Imidazole → 4-(2-{[Tert-butyl(dimethyl)silyl]oxy}ethoxy)-2-chloropyrimidine

HRID 410708ノート

反応式

HRID 410708 の反応式
N1C=CN=C1.[Cl:6][C:7]1[N:12]=[C:11]([O:13][CH2:14][CH2:15][OH:16])[CH:10]=[CH:9][N:8]=1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>ClCCl>[Si:17]([O:16][CH2:15][CH2:14][O:13][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([Cl:6])[N:12]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 597640682-[(2-Chloropyrimidin-4-yl)oxy]ethanol

生成物 1

HCID 866582614-(2-{[Tert-butyl(dimethyl)silyl]oxy}ethoxy)-2-chloropyrimidine収率 99%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Imidazole (389 mg, 5.72 mmol) was added to a suspension of 2-[(2-chloropyrimidin-4-yl)oxy]ethanol (416 mg, 2.38 mmol) in dichloromethane (9.5 mL) at 0° C. tert-Butyldimethylsilyl chloride (424 mg, 2.81 mmol) was added and the reaction mixture stirred at room temperature for 2 h. The reaction was quenched with water and the organic layer separated. The organic layer was dried over sodium sulfate, filtered, and concentrated to give 4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)-2-chloropyrimidine (678 mg, 2.35 mmol, 99% yield) as a clear, yellow oil. MS ESI: [M+H]+ m/z 289.1.

後処理

  1. additionwas added
  2. customThe reaction was quenched with water
  3. customthe organic layer separated
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-1664ba557db24ec4a2aa7f4959c404c6
出典データセット
uspto-grants-2014_06
特許番号
US08759366B2

反応ノート

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