Benzenepropanoic acid → N-[4-(3-chlorophenyl)-6-methyl-2-(methylthio)-5-pyrimidinyl]-3-phenylpropanamide

HRID 1182618

Reaktionsgleichung

Reaktionsgleichung von HRID 1182618
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C.[Cl:17][C:18]1[CH:19]=[C:20]([C:24]2[C:29]([NH2:30])=[C:28]([CH3:31])[N:27]=[C:26]([S:32][CH3:33])[N:25]=2)[CH:21]=[CH:22][CH:23]=1.N1C=CC=CC=1>S(Cl)(Cl)=O>[Cl:17][C:18]1[CH:19]=[C:20]([C:24]2[C:29]([NH:30][C:9](=[O:11])[CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:28]([CH3:31])[N:27]=[C:26]([S:32][CH3:33])[N:25]=2)[CH:21]=[CH:22][CH:23]=1

Komponenten

6

Edukt 4

HCID 107Benzenepropanoic acidHCID 1049PyridineHCID 6228DimethylformamideHCID 178545764-(3-Chlorophenyl)-6-methyl-2-(methylthio)-5-pyrimidinamine

Produkt 1

HCID 58981790N-[4-(3-chlorophenyl)-6-methyl-2-(methylthio)-5-pyrimidinyl]-3-phenylpropanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

51.4 mg (0.342 mmol) of 3-phenylpropionic 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-66f52f258fbd4456b5b8f6c5ff0a6088
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288544B2

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