Uracil → 1-[2-(2,2-Dimethyl-1,3-dioxan-5-yl)ethyl]uracil

HRID 908527

Reaktionsgleichung

Reaktionsgleichung von HRID 908527
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:16][CH2:17][CH:18]1[CH2:23][O:22][C:21]([CH3:25])([CH3:24])[O:20][CH2:19]1>CN(C=O)C>[CH3:24][C:21]1([CH3:25])[O:22][CH2:23][CH:18]([CH2:17][CH2:16][N:1]2[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]2=[O:3])[CH2:19][O:20]1

Komponenten

5

Edukt 3

HCID 1174UracilHCID 10796Cesium carbonateHCID 1789881,3-Dioxane, 5-(2-bromoethyl)-2,2-dimethyl-

Produkt 1

HCID 578389791-[2-(2,2-Dimethyl-1,3-dioxan-5-yl)ethyl]uracilAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of uracil (88.5 g, 0.79 mol) in dry DMF (250 mL) was added cesium carbonate (171 g, 0.527 mol) at RT and stirred at the same temperature for 30 min. To the above reaction mixture was added a solution of compound 33 (117 g, 0.527 mol) in dry DMF (250 mL) over a period of 30 min and heated at 50° C. for 24 h. The reaction mixture was filtered, filtrate concentrated under vacuum and crude purified by column chromatography over silica gel (3% methanol in chloroform) to give the title compound (60 g, 45%). TLC: Chloroform/Methanol, 4:1, Rf=0.3

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationfiltrate concentrated under vacuum and crude
  3. custompurified by column chromatography over silica gel (3% methanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-b0c9446791bd4fca8105e0ad0917d13a
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017620B2

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