Water → 2-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetic acid

HRID 927217Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 927217
[OH-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[N:16]([CH2:17][C:18]([O:20]C)=[O:19])[C:15](=[O:22])[N:14]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[C:13]3[CH2:33][CH2:34][C:35](=[O:36])[C:12]2=3)=[CH:7][CH:6]=1)#[N:4].O>O1CCCC1>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[N:16]([CH2:17][C:18]([OH:20])=[O:19])[C:15](=[O:22])[N:14]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:30])[F:31])[CH:24]=3)[C:13]3[CH2:33][CH2:34][C:35](=[O:36])[C:12]2=3)=[CH:9][CH:10]=1)#[N:4]

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 90310893Methyl 2-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetate

Produkt 1

HCID 903109622-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Aqueous sodium hydroxide solution (1 M, 15.0 mL, 15.0 mmol) is added to a solution of methyl 2-(4-(4-cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetate (example 3, 2.64 g, 5.62 mmol) in tetrahydrofuran (40 mL) and the mixture is stirred at room temperature for 4 h. Water is added and the mixture is extracted three times with ethyl acetate. The aqueous layer is acidified a) with hydrogen chloride and extracted twice with dichloromethane. These organic layers are combined and concentrated. Yield: 1.84 g; ESI mass spectrum [M+H]+=456; Retention time HPLC: 0.84 min (Z018_S04).

Aufarbeitung

  1. extractionthe mixture is extracted three times with ethyl acetate
  2. extractionextracted twice with dichloromethane
  3. concentrationconcentrated
  4. custom0.84 min (Z018_S04)

Quellen und Nachweise

ORD-Eintrag
ord-38068efda92f4ec0ad1bee4e8cb324b7
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290459B1

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