Ethyl bromoacetate → HCID 59336109, compound

HRID 2359463Notes

Reaction equation

HRID 2359463 reaction equation
[F:1][C:2]1[C:3]([NH2:9])=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>CN(C)C=O>[NH2:9][C:3]1[C:2]([F:1])=[CH:7][N:6]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5](=[O:8])[N:4]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178509021HCID 178509021, compound

Product 1

HCID 59336109HCID 59336109, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-Fluorocytosine (500 mg) and potassium carbonate (803 mg) were suspended in N,N-dimethylformamide (5 mL) and ethyl bromoacetate (430 μL) was added to the suspension. The mixture was stirred at 100° C. overnight. The resulting precipitate was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (methylene chloride: methanol=99:1 to 92:9) to give 329 mg (39% yield) of the desired product as a white amorphous.

Workup

  1. customThe resulting precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (methylene chloride: methanol=99:1 to 92:9)

Sources & evidence

ORD record
ord-20d841a9e86740a4abc6abd23bd87006
Source dataset
uspto-grants-2014_04
Patent number
US08685989B2

Reaction notes

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