Ethyl Acetate → 7-(1-acetylthioethyl)-4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-one

HRID 368993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 368993
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].Br[CH:7]([C:9]1[CH:10]=[CH:11][C:12]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)=[N:16][C:15](=[O:25])[N:14]([CH2:26][CH3:27])[C:13]=2[N:28]=1)[CH3:8].C(OCC)(=O)C>CN(C)C=O>[C:1]([S:3][CH:7]([C:9]1[CH:10]=[CH:11][C:12]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)=[N:16][C:15](=[O:25])[N:14]([CH2:26][CH3:27])[C:13]=2[N:28]=1)[CH3:8])(=[O:4])[CH3:2]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 232844947-(1-bromoethyl)-4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-oneHCID 23670855Potassium ethanethioate

Produkt 1

HCID 154615797-(1-acetylthioethyl)-4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-oneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Potassium thioacetate (0.54 g, 48 mmol) was added to 7-(1-bromoethyl)-4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-one (1.57 g, 40 mmol) dissolved in dimethylformamide (16 ml), followed by stirring at room temperature for 2 hours. The reaction solution was mixed with ethyl acetate, washed with water and with brine, and dried over anhydrous magnesium sulfate. The magnesium sulfate was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 7-(1-acetylthioethyl)-4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-one (1.13 g, 73%).

Aufarbeitung

  1. washwashed with water and with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe magnesium sulfate was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1ce993c6369149ec98c43ae637205a51
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06136810

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