Pyridine → N-[4-(3-chlorophenyl)-6-methyl-2-(methylthio)-5-pyrimidinyl]-4-phenylbutanamide

HRID 1182619

Reaktionsgleichung

Reaktionsgleichung von HRID 1182619
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C.[Cl:18][C:19]1[CH:20]=[C:21]([C:25]2[C:30]([NH2:31])=[C:29]([CH3:32])[N:28]=[C:27]([S:33][CH3:34])[N:26]=2)[CH:22]=[CH:23][CH:24]=1.N1C=CC=CC=1>S(Cl)(Cl)=O>[Cl:18][C:19]1[CH:20]=[C:21]([C:25]2[C:30]([NH:31][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:29]([CH3:32])[N:28]=[C:27]([S:33][CH3:34])[N:26]=2)[CH:22]=[CH:23][CH:24]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 47754-Phenylbutyric AcidHCID 6228DimethylformamideHCID 178545764-(3-Chlorophenyl)-6-methyl-2-(methylthio)-5-pyrimidinamine

Produkt 1

HCID 58981796N-[4-(3-chlorophenyl)-6-methyl-2-(methylthio)-5-pyrimidinyl]-4-phenylbutanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

56.2 mg (0.342 mmol) of 4-phenylbutyric acid was dissolved in 1 ml of thionyl chloride. A catalytic amount of DMF was added and stirred at room temperature for 3 hours. After the solvent was evaporated under reduced pressure, 45.4 mg (0.171 mmol) of 4-(3-chlorophenyl)-6-methyl-2-(methylthio)-5-pyrimidinamine and 1 ml of pyridine were added and stirred at 50° C. overnight. After the solvent was evaporated under reduced pressure, the reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1) to obtain the title compound.

Aufarbeitung

  1. additionwere added
  2. stirringstirred at 50° C. overnight
  3. customAfter the solvent was evaporated under reduced pressure
  4. additionthe reaction mixture was diluted with ethyl acetate
  5. washwashed with saturated aqueous sodium chloride solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1)

Quellen und Nachweise

ORD-Eintrag
ord-1116d4ee77e54c108accd29066fc448a
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288544B2

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