Water → HCID 178518706, compound

HRID 326869Notes

Reaction equation

HRID 326869 reaction equation
C([O:4][CH2:5][C:6]1[NH:15][C:14](=[O:16])[C:13]2[C:8](=[N:9][C:10]([OH:17])=[CH:11][N:12]=2)[N:7]=1)(=O)C.[OH-].[K+].O>C(O)C>[OH:17][C:10]1[N:9]=[C:8]2[C:13]([C:14](=[O:16])[NH:15][C:6]([CH2:5][OH:4])=[N:7]2)=[N:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 178475914HCID 178475914, compound

Product 1

HCID 178518706HCID 178518706, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.0 g (0.0169 mole) of 2-acetoxymethyl-7-hydroxy-4(3H)-pteridinone, 1.2 g (0.0214 mole) of potassium hydroxide and 5 ml of water in 80 ml of ethanol is refluxed for 4 hours. After cooling, the reaction mixture is filtered. The solid thereby isolated is washed with 30 ml of ethanol and taken up in 160 ml of water. The cloudy solution obtained is clarified by filtration and acidified with acetic acid to pH 3.6. The precipitate formed is isolated by filtration. It is purified by washing with ether and recrystallization from a mixture of ethanol and N,N-dimethylformamide. Yld: 2.0 g (61%), m.p. >300° C.

Workup

  1. temperatureis refluxed for 4 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered
  4. customThe solid thereby isolated
  5. washis washed with 30 ml of ethanol
  6. customThe cloudy solution obtained
  7. filtrationis clarified by filtration
  8. customThe precipitate formed
  9. customis isolated by filtration
  10. customIt is purified
  11. washby washing with ether and recrystallization from a mixture of ethanol and N,N-dimethylformamide

Sources & evidence

ORD record
ord-83a322adf6814fea98a95b818bcb7aa2
Source dataset
uspto-grants-1993_12
Patent number
US05270465

Reaction notes

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