Water → HCID 86657016, Verbindung

HRID 467441

Reaktionsgleichung

Reaktionsgleichung von HRID 467441
[F:1][C:2]([F:16])([F:15])[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=1)=[O:4].[H-].[Na+].Cl[C:20]1[N:25]=[C:24]([NH2:26])[CH:23]=[CH:22][N:21]=1.O>CC(N(C)C)=O>[NH2:26][C:24]1[CH:23]=[CH:22][N:21]=[C:20]([O:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][NH:5][C:3](=[O:4])[C:2]([F:15])([F:16])[F:1])=[CH:8][CH:9]=2)[N:25]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3457522-Chloro-4-aminopyrimidineHCID 158522092,2,2-Trifluoro-N-{[4-(hydroxymethyl)phenyl]methyl}acetamide

Produkt 1

HCID 86657016HCID 86657016, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

760 mg (3.25 mmol) 2,2,2-Trifluoro-N-(4-hydroxymethyl-benzyl)-acetamide is dissolved in 3 mL dry dimethylacetamide under argon atmosphere, and 273 mg (8.15 mmol) NaH is added over 5 min. 211 mg (1.63 mmol) 2-Chloropyrimidin-4-amine is then added and the solution stirred at 90° C. over night. 1 mL Water is added carefully to quench all excess NaH, and the mixture poured into 50 ml of 0.5 N HCl. The crude product is extracted with ethyl acetate, the combined organic phases washed with brine and dried over MgSO4. After evaporation of the solvent, the product is purified by flash column chromatography (gradient ethyl acetate:cyclohexane from 1:1 to 3:1). Yield: 350 mg (52%). ESI-MS m/z 327 [M+H]+.

Aufarbeitung

  1. customto quench all excess NaH
  2. additionthe mixture poured into 50 ml of 0.5 N HCl
  3. extractionThe crude product is extracted with ethyl acetate
  4. washthe combined organic phases washed with brine
  5. dry with materialdried over MgSO4
  6. customAfter evaporation of the solvent
  7. customthe product is purified by flash column chromatography (gradient ethyl acetate:cyclohexane from 1:1 to 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-78a6119b1f294db78f88c5a6f32d9db6
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623627B2

Verknüpfte Notizen

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