Ethyl Acetate → 4-chloro-2-(N-cyano-N-methylamino)-6-[(4-methyl)-piperidin-1-yl]-5-phenylpyrimidine

HRID 496303

Reaktionsgleichung

Reaktionsgleichung von HRID 496303
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([N:14]2[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]2)[N:5]=[C:4](S(C)(=O)=O)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:31][NH:32][C:33]#[N:34].C(OCC)(=O)C>CN(C)C=O.O>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([N:14]2[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]2)[N:5]=[C:4]([N:32]([C:33]#[N:34])[CH3:31])[N:3]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 119415MethylcyanamideHCID 223254954-Chloro-6-[(4-methyl)-piperidin-1-yl]-2-methylsulfonyl-5-phenyl-pyrimidine

Produkt 1

HCID 223254994-chloro-2-(N-cyano-N-methylamino)-6-[(4-methyl)-piperidin-1-yl]-5-phenylpyrimidineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-6-[(4-methyl)-piperidin-1-yl]-2-methylsulfonyl-5-phenyl-pyrimidine (0.5 g, 1.37 mmol) in dimethylformamide (6 ml) was added potassium carbonate (0.38 g, 2.73 mmol) followed by methyl cyanamide (0.31 g, 5.47 mmol). After stirring the reaction mixture at room temperature for 19 hours the reaction mixture was diluted with water (75 ml), and extracted with ethyl acetate (75 ml). The organic phase was washed with water (75 ml), followed by saturated brine (75 ml), dried over magnesium sulfate and concentrated in vacuo to afford a yellow syrup. The crude product was chromatographed an silica gel eluting with 90:10 v/v hexane:ethyl acetate to afford 0.39 g (84% yield) of the title compound as a cololess syrup.

Aufarbeitung

  1. extractionextracted with ethyl acetate (75 ml)
  2. washThe organic phase was washed with water (75 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto afford a yellow syrup
  6. customThe crude product was chromatographed an silica gel eluting with 90:10 v/v hexane

Quellen und Nachweise

ORD-Eintrag
ord-95ad2a90ea6f404d9a72b60038922dc4
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06943252B2

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