Ethyl bromoacetate → 6-Amino-3-carboethoxymethyl-1-propyluracil

HRID 1682101Notes

Reaction equation

HRID 1682101 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[NH:5][C:4](=[O:12])[CH:3]=1.[H-].[Na+].[H][H].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>O>[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[N:5]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:4](=[O:12])[CH:3]=1

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 1045626-Amino-1-propyluracilHCID 178418361HCID 178418361, compound

Product 1

HCID 198046626-Amino-3-carboethoxymethyl-1-propyluracil

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

6-Amino-1-propyluracil (10 g, 59.1 mmol) was dissolved by warming gently in 60 mL of dimethylsufoxide. 2.0 g (66 mmol) of an 80% dispersion of sodium hydride in mineral oil was added in portions to the solution while stirring under argon. After the evolution of hydrogen ceased, the mixture was heated to 40° C. until a solution resulted. To this solution at 25° C. was added ethyl bromoacetate (7.1 mL, 62 mmol), with the mixture maintained under argon at room temperature for 44 hours. The mixture was then diluted with 200 mL of water and extracted with hexane to remove the mineral oil. The aqueous layer was adjusted to pH 10 with 3N sodium hydroxide and extracted with dichloromethane. The extracts were dried over anhydrous sodium sulfate and concentrated to a brown liquid, which was purified by flash chromatography (silica gel, 9:1/chloroform:ethanol) to yield a crystalline product.

Workup

  1. temperatureby warming gently in 60 mL of dimethylsufoxide
  2. customresulted
  3. temperaturewith the mixture maintained under argon at room temperature for 44 hours
  4. extractionextracted with hexane
  5. customto remove the mineral oil
  6. extractionextracted with dichloromethane
  7. dry with materialThe extracts were dried over anhydrous sodium sulfate
  8. concentrationconcentrated to a brown liquid, which
  9. customwas purified by flash chromatography (silica gel, 9:1/chloroform:ethanol)
  10. customto yield a crystalline product

Sources & evidence

ORD record
ord-c953f353423d4846b83cd90330e1c42b
Source dataset
uspto-grants-1992_12
Patent number
US05175290

Reaction notes

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