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

HRID 732920

Reaktionsgleichung

Reaktionsgleichung von HRID 732920
Br[CH2:2][CH2:3][CH:4]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[O:6][CH2:5]1.[NH:12]1[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]1=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:10][C:7]1([CH3:11])[O:8][CH2:9][CH:4]([CH2:3][CH2:2][N:12]2[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]2=[O:14])[CH2:5][O:6]1

Komponenten

5

Edukt 3

HCID 1174UracilHCID 11430Potassium 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 29,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 5-(2-bromoethyl)-2,2-dimethyl-1,3-dioxane (15) (M. R. Harnden et al, J. Med. Chem., 30, 1636, 1987) (12.0 gm, 53.81 mmol) in dry DMF (150 ml) were added uracil (7.0 gm, 62.4 mmol) and potassium carbonate (14.0 gm). The reaction mixture was stirred at 25° C. for 5 days. The resulting solution was filtered and the solvent removed. The residue obtained was purified by column chromatography on silica gel eluting with chloroform-methanol (90:10, v/v) to afford 17 (4.0 gm, 25.2%).

Aufarbeitung

  1. filtrationThe resulting solution was filtered
  2. customthe solvent removed
  3. customThe residue obtained
  4. customwas purified by column chromatography on silica gel eluting with chloroform-methanol (90:10

Quellen und Nachweise

ORD-Eintrag
ord-dadfa1e4456d4d92a61eb34f1130e36d
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589077B2

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