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

HRID 410708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 410708
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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1664ba557db24ec4a2aa7f4959c404c6
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759366B2

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