Dichloromethane → HCID 44220300, Verbindung

HRID 237382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 237382
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]([NH:9][C:10]([C:12]1[S:30][C:15]2[N:16]=[C:17]([NH2:29])[N:18]=[C:19]([C:20]3[CH:25]=[C:24]([OH:26])[C:23]([Cl:27])=[CH:22][C:21]=3[Cl:28])[C:14]=2[CH:13]=1)=[O:11])[CH3:8].ClCCl.Br.Br[CH2:36][CH2:37][N:38]([CH2:41][CH3:42])[CH2:39][CH3:40]>CN(C=O)C>[CH2:7]([NH:9][C:10]([C:12]1[S:30][C:15]2[N:16]=[C:17]([NH2:29])[N:18]=[C:19]([C:20]3[CH:25]=[C:24]([O:26][CH2:36][CH2:37][N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[C:23]([Cl:27])=[CH:22][C:21]=3[Cl:28])[C:14]=2[CH:13]=1)=[O:11])[CH3:8]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 706072-Bromoethyldiethylammonium bromideHCID 44220298HCID 44220298, Verbindung

Produkt 1

HCID 44220300HCID 44220300, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-140 °C

Versuchsvorschrift

Cesium carbonate was added to a solution of 2-Amino-4-(2,4-dichloro-5-hydroxyphenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl amide in DMF, 2-Bromo-N,N-diethylethylamine hydrobromide was added and the suspension heated, at −140° C., for ˜2 hrs. The resulting suspension was allowed to cool and dichloromethane added. The mixture was washed with water and saturated aqueous sodium chloride solution. The solution was dried over anhydrous sodium sulphate and concentrated to a dark brown gum. The crude product was purified by chromatography on silica eluting with mixtures of dichloromethane and methanol.

Aufarbeitung

  1. additionwas added
  2. temperatureto cool
  3. washThe mixture was washed with water and saturated aqueous sodium chloride solution
  4. dry with materialThe solution was dried over anhydrous sodium sulphate
  5. concentrationconcentrated to a dark brown gum
  6. customThe crude product was purified by chromatography on silica eluting with mixtures of dichloromethane and methanol

Quellen und Nachweise

ORD-Eintrag
ord-b99ec7c7e4ed4765b80750c6bbcafd16
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642594B2

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