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

HRID 65915Notes

Reaction equation

HRID 65915 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-hydroxyaminouracil, 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-236fd08383f64e2cb363e09d99783ced
Source dataset
uspto-grants-1978_12
Patent number
US04129654

Reaction notes

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