1,3-Dimethyl-6-hydroxylaminouracil → Isoxazolo(3,4-d)pyrimidine-4,6(5H,7H)-dione, 5,7-dimethyl-

HRID 1395269Notes

Reaction equation

HRID 1395269 reaction equation
[CH3:1][N:2]1[C:9]([NH:10][OH:11])=[CH:8][C:6](=[O:7])[N:5]([CH3:12])[C:3]1=[O:4].[CH:13]([O-])([O-])OCC>CN(C)C=O>[CH3:12][N:5]1[C:6](=[O:7])[C:8]2=[CH:13][O:11][N:10]=[C:9]2[N:2]([CH3:1])[C:3]1=[O:4]

Participants

4

Reactant 2

HCID 27859331,3-Dimethyl-6-hydroxylaminouracilHCID 53630039Ethylorthoformate

Product 1

HCID 2785556Isoxazolo(3,4-d)pyrimidine-4,6(5H,7H)-dione, 5,7-dimethyl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2 g of 1,3-dimethyl-6-hydroxyamino-uracil, 20 ml of dimethylformamide and 20 ml of ethyl orthoformate is boiled at 160° C. for 1 hour, after which the solvent is distilled off. To the residue is added ethanol and the resultant crystals are collected by filtration. As recrystallized from hot water, 1.0 g of the captioned compound is obtained as colorless prisms, melting point: 170°-171° C.

Workup

  1. customfor 1 hour
  2. distillationafter which the solvent is distilled off
  3. additionTo the residue is added ethanol
  4. filtrationthe resultant crystals are collected by filtration
  5. customAs recrystallized from hot water

Sources & evidence

ORD record
ord-4a658b113ab34ca394cde5cbd686fe57
Source dataset
uspto-grants-1980_05
Patent number
US04202975

Reaction notes

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