Glyoxal → 4-Ethoxypteridin-2-amine

HRID 1784108Notes

Reaction equation

HRID 1784108 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][CH3:10])[C:5]([NH2:11])=[C:4]([NH2:12])[N:3]=1.[CH:13]([CH:15]=O)=O>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][CH3:10])[C:5]2[C:4](=[N:12][CH:13]=[CH:15][N:11]=2)[N:3]=1

Participants

4

Reactant 2

HCID 7860GlyoxalHCID 135414226-Ethoxypyrimidine-2,4,5-triamine

Product 1

HCID 113675134-Ethoxypteridin-2-amineYield 206.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,5,6-triamino-4-ethoxy-pyrimidine (10.54 g, 62.37 mmoles) in ethanol (160 ml) was added glyoxal (40% solution in water, 2.7 ml, 18.6 mmoles). The reaction mixture was refluxed for 4 hours. Some insoluble material was filtered off. The filtrate was concentrated in vacuo and the residue purified by flash chromatography (silica, using a CH3OH/CH2Cl2 mixture (5:95) as the eluent), providing the pure title compound (7.34 g, yield: 62%). The spectral data of the product are identical with the literature data (W. Pfleiderer et al. cited supra).

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. filtrationSome insoluble material was filtered off
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue purified by flash chromatography (silica

Sources & evidence

ORD record
ord-ab953b8828c14caebd4e517da3330303
Source dataset
uspto-grants-2009_03
Patent number
US07501513B2

Reaction notes

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