Selenium Dioxide → HCID 13060225, compound

HRID 1075277Notes

Reaction equation

HRID 1075277 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:5]=[C:4]([NH:14][CH:15]=[O:16])[CH:3]=1.[Se](=O)=[O:18]>CN(C)C=O>[Cl:1][C:2]1[N:7]=[C:6]([C:8](=[O:18])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:5]=[C:4]([NH:14][CH:15]=[O:16])[CH:3]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 23316850HCID 23316850, compound

Product 1

HCID 13060225HCID 13060225, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 2-(6-chloro-4-formamidopyrimidin-2-yl)acetate (24.3 g) and selenium dioxide (16.65 g) in N,N-dimethylformamide (243 ml) was stirred for an hour at 70° to 75° C. The precipitated solid was filtered off, and the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate (500 ml), washed with water and an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was triturated with diisopropyl ether to give a powder of ethyl 6-chloro-4-formamidopyrimidin-2-ylglyoxylate (17.74 g).

Workup

  1. filtrationThe precipitated solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (500 ml)
  4. washwashed with water
  5. dry with materialan aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-b613982aff9d47d7848c159daf6b849b
Source dataset
uspto-grants-1983_07
Patent number
US04395411

Reaction notes

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