Uracil → 1-Benzyluracil

HRID 1744760

Reaktionsgleichung

Reaktionsgleichung von HRID 1744760
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C>[CH2:15]([N:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 1174UracilHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Produkt 1

HCID 2379621-BenzyluracilAusbeute 14,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 10 g (89 mmol) of uracil and 24.6 g of potassium carbonate in 350 mL DMF was stirred for 12 hours at room temperature, after which 16.5 mL (139 mmol) of benzyl bromide was added and the reaction allowed to continue for 2 days at room temperature. The undissolved residue was removed by filtration and the solvent removed from the filtrate under reduced pressure. 150 mL water was added to the residue and the mixture extracted 3 times with 100 mL methylene chloride. The collected methylene chloride fractions were washed with water, dried over MgSO4 and evaporated to dryness under reduced pressure. The residue was treated with a small amount of chloroform/methanol 40:1 from which 1-benzyluracil partially crystallizes. 2.6 g 1-benzyluracil was isolated by filtration and the rest was isolated by preparative column chromatography, using chloroform/methanol 40:1 giving a yield of 3.95 g (22%)(m.p. 168–170° C., Lit. 168–170° C., Kundu et al., J. Chem. Soc. Perkin Trans 1, 1985, 1295).

Aufarbeitung

  1. waitto continue for 2 days at room temperature
  2. customThe undissolved residue was removed by filtration
  3. customthe solvent removed from the filtrate under reduced pressure
  4. addition150 mL water was added to the residue
  5. extractionthe mixture extracted 3 times with 100 mL methylene chloride
  6. washThe collected methylene chloride fractions were washed with water
  7. dry with materialdried over MgSO4
  8. customevaporated to dryness under reduced pressure
  9. additionThe residue was treated with a small amount of chloroform/methanol 40:1 from which 1-benzyluracil
  10. custompartially crystallizes

Quellen und Nachweise

ORD-Eintrag
ord-e0c3c91c89914ec0a34162508b09d9fa
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07018786B2

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