Chloromethyl ethyl ether → 1-Ethoxymethyl-5-ethyluracil

HRID 2210905Notes

Reaction equation

HRID 2210905 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[Si](C([Si](C)(C)C)C(N)=O)(C)C.[CH2:23]([O:25][CH2:26]Cl)[CH3:24].C(=O)(O)[O-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH2:23]([O:25][CH2:26][N:7]1[CH:8]=[C:3]([CH2:1][CH3:2])[C:4](=[O:10])[NH:5][C:6]1=[O:9])[CH3:24]

Participants

7

Reactant 4

HCID 18523Chloromethyl ethyl etherHCID 732675-Ethyl-2,4(1H,3H)-pyrimidinedioneHCID 516892Sodium BicarbonateHCID 11708267Bistrimethylsilylacetamid

Product 1

HCID 102623171-Ethoxymethyl-5-ethyluracilYield 81%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Procedure

To 100 ml of methylene chloride, 5.1 g (40 mmol) of 5-ethyluracil and 22 ml (88 mmol) of bistrimethylsilylacetamide were added under a nitrogen atmosphere and stirred for 40 minutes at room temperature. To this mixture, 4.1 ml (88 mmole) of chloromethyl ethyl ether and 0.15 g (0.4 mmol) of tetrabutylammonium iodide were added and heated under reflux for 15 hours. Then, the reaction mixture was poured into 50 ml of saturated sodium bicarbonate solution carefully and filtered through Celite. The organic layer was washed with water, dried on magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from ethyl acetate to obtain 6.4 g of 1-ethoxymethyl-5-ethyluracil (Yield: 81%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 15 hours
  3. filtrationfiltered through Celite
  4. washThe organic layer was washed with water
  5. customdried on magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-8dd0c1cbc89c4ea9aed35b6144c66df4
Source dataset
uspto-grants-1995_10
Patent number
US05461060

Reaction notes

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