Potassium Carbonate → 1-Butyl-5-ethyluracil

HRID 2210906Notes

Reaction equation

HRID 2210906 reaction equation
[CH2:1]([C:3]1[C:4](=[O:10])[NH:5][C:6](=[O:9])[NH:7][CH:8]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:2]([N:7]1[CH:8]=[C:3]([CH2:1][CH3:2])[C:4](=[O:10])[NH:5][C:6]1=[O:9])[CH2:1][CH2:3][CH3:8]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 732675-Ethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 186710321-Butyl-5-ethyluracilYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5.6 g (40 mmol) of 5-ethyluracil in 60 ml of dimethylformamide, 5.5 g (40 mmol) of potassium carbonate and 2.3 ml (20 mmol) of n-iodobutane were added and stirred for 2 hours at 120° C. The reaction mixture was concentrated under reduced pressure and distributed between dichloromethane and aqueous solution of ammonium chloride, and the organic layer was concentrated under reduced pressure. The residue was adsorbed on a silica gel column and eluted with 30% ethyl acetate/hexane to obtain 2.7 g of 1-butyl-5-ethyluracil (Yield: 69%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. washeluted with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-3dd260fca83644888c8129a9a3da51e5
Source dataset
uspto-grants-1995_10
Patent number
US05461060

Reaction notes

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