Carbamic acid, ethyl ester → Ethyl (4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]methyl}pyridin-2-yl)carbamate

HRID 546593

Reaktionsgleichung

Reaktionsgleichung von HRID 546593
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22](Cl)[CH:21]=3)[C:12]2=[O:27])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[C:34](=[O:39])([O:36][CH2:37][CH3:38])[NH2:35]>O1CCOCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:35][C:34](=[O:39])[O:36][CH2:37][CH3:38])[CH:21]=3)[C:12]2=[O:27])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 5641Carbamic acid, ethyl esterHCID 10796Cesium carbonateHCID 576259713-(4-Tert-butylphenyl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione

Produkt 1

HCID 57626004Ethyl (4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]methyl}pyridin-2-yl)carbamateAusbeute 45,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

To a solution of 3.5 g of 3-(4-tert-butylphenyl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione obtained in stage a) of Example 7 in 90 mL of dioxane are successively added, under argon, 406 mg of palladium diacetate, 1.1 g of (9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine)[xantphos], 12.9 g of caesium carbonate and 1.86 g of ethyl carbamate. The reaction mixture is heated at 105° C. for 7 hours, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with a mixture of cyclohexane and ethyl acetate (60/40 by volume) to give 1.8 g of ethyl (4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]methyl}pyridin-2-yl)carbamate, the characteristics of which are as follows:

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is purified by chromatography on a column of silica
  4. washeluting with a mixture of cyclohexane and ethyl acetate (60/40 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-ca7f9b45c9ca43c482cc2688da6f020a
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935819B2

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