Ethyl bromoacetate → Ethyl 2-(4,6-dimethylpyrimidin-2-yl)oxyacetate

HRID 847117

Reaction equation

HRID 847117 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[N:7]=[C:2]([O:1][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 95084,6-Dimethylpyrimidin-2-olHCID 11430Potassium Carbonate

Product 1

HCID 3410252Ethyl 2-(4,6-dimethylpyrimidin-2-yl)oxyacetateYield 26.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-4,6-dimethyl pyrimidine (10g, 0.08 mol) was dissolved in 150ml of dimethylformamide. Ethyl bromoacetate (13.5g, 0.08 mol) was added and also, subsequently, 11.lg of potassium carbonate. The reaction mixture was refluxed overnight. A precipitate had formed which was filtered off and the solvent was then evaporated off from the filtrate to form a crude oily product. Following purification by flash chromatography, 4.5g of the title product were obtained in the form of a red oil.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customA precipitate had formed which
  3. filtrationwas filtered off
  4. customthe solvent was then evaporated off from the filtrate
  5. customto form a crude oily product
  6. custompurification by flash chromatography

Sources & evidence

ORD record
ord-83d2bb0b404543c793d87e333bd2852c
Source dataset
uspto-grants-1992_08
Patent number
US05139563

Linked notes

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