Uracil → 1-allyluracil

HRID 1744759Notes

Reaction equation

HRID 1744759 reaction equation
[H-].[Na+].[NH:3]1[CH:10]=[CH:9][C:7](=[O:8])[NH:6][C:4]1=[O:5].[CH2:11](Br)[CH:12]=[CH2:13]>CN(C=O)C>[CH2:13]([N:3]1[CH:10]=[CH:9][C:7](=[O:8])[NH:6][C:4]1=[O:5])[CH:12]=[CH2:11]

Participants

5

Reactant 3

HCID 1174UracilHCID 7841Allyl bromideHCID 24758Sodium hydride

Product 1

HCID 2958571-allyluracilYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

2.5 g (104 mmol, 80% suspension) of NaH was added to a suspension of 10.5 g (93 mmol) uracil in 100 ml DMF and the reaction allowed to continue for 2 hours at room temperature. After 2 hours 10.73 mL (15 g, 123 mmol) allylbromide was added and the mixture heated for 2 hours at 70° C. The solvent was removed under reduced pressure and the residue treated with methylene chloride. The residue from the methylene chloride extract was a mixture of mono-allyl- and di-allyl-uracil. 5.5 g (39%) of 1-allyluracil was isolated by preparative column chromatography, using chlormoform/methanol 40:1 as eluant (m.p. 108–109° C., Lit. 105–109° C., Beilstein).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue treated with methylene chloride
  3. extractionThe residue from the methylene chloride extract
  4. additiona mixture of mono-allyl- and di-allyl-uracil

Sources & evidence

ORD record
ord-a661119c6c6f477eb45b2d396ca5d29f
Source dataset
uspto-grants-2006_03
Patent number
US07018786B2

Reaction notes

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