Pyridine → [1-(2,2-Dimethylpropionyloxymethyl)-7-(2-formylphenyl)-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl 2,2-dimethylpropionate

HRID 1792079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1792079
[CH3:1][C:2]([CH3:27])([CH3:26])[C:3]([O:5][CH2:6][N:7]1[C:15]2[N:14]=[CH:13][NH:12][C:11]=2[C:10](=[O:16])[N:9]([CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[C:8]1=[O:25])=[O:4].[CH:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O)=[O:29].N1C=CC=CC=1>CN(C)C=O.C(OCC)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:22][C:20]([CH3:21])([CH3:23])[C:19]([O:18][CH2:17][N:9]1[C:10](=[O:16])[C:11]2[N:12]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[CH:28]=[O:29])[CH:13]=[N:14][C:15]=2[N:7]([CH2:6][O:5][C:3](=[O:4])[C:2]([CH3:27])([CH3:26])[CH3:1])[C:8]1=[O:25])=[O:24]

Komponenten

7

Edukt 3

HCID 1049PyridineHCID 2921892-Formylphenylboronic acidHCID 153324012,2-Dimethylpropionic acid [3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester

Produkt 1

HCID 23536861[1-(2,2-Dimethylpropionyloxymethyl)-7-(2-formylphenyl)-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl 2,2-dimethylpropionateAusbeute 31,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8895Cupric acetateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2,2-Dimethylpropionic acid [3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester (10.2 g), 2-formylphenylboronic acid (8.04 g), and copper(II) acetate (7.30 g) were suspended in N,N-dimethylformamide (50 ml), pyridine (4.34 ml) was added thereto, and the mixture was stirred at room temperature for 37 hours. The reaction mixture was diluted with ethyl acetate; and washed with water. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to give 4.12 g of the title compound from the elution fraction of hexane-ethyl acetate (1:2).

Aufarbeitung

  1. washand washed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-05e81e29142c4ae0868982a133fee016
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074798B2

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