Methyl iodide → 7-Cyclohexyl-5-methyl-5H,7H-isoxazolo[3,4-d]pyrimidine-4,6-dione

HRID 65917Notes

Reaction equation

HRID 65917 reaction equation
[CH:1]1([N:7]2[C:12]3=[N:13][O:14][CH:15]=[C:11]3[C:10](=[O:16])[NH:9][C:8]2=[O:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:18](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH:1]1([N:7]2[C:12]3=[N:13][O:14][CH:15]=[C:11]3[C:10](=[O:16])[N:9]([CH3:18])[C:8]2=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 135369437-cyclohexyl-5H,7H-isoxazolo[3,4-d]pyrimidine-4,6-dione

Product 1

HCID 123806247-Cyclohexyl-5-methyl-5H,7H-isoxazolo[3,4-d]pyrimidine-4,6-dioneYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 50 ml of dimethylformamide is dissolved 1 g of the 7-cyclohexyl-5H,7H-isoxazolo[3,4-d]pyrimidine-4,6-dione obtained in Example 18, followed by addition of 800 mg of potassium carbonate and 1 ml of methyl iodide. The mixture is stirred at room temperature for 20 hours, after which the insolubles are filtered off. The filtrate is concentrated to dryness and the concentrate is dissolved in chloroform. After the insolubles are filtered off, the chloroform is removed by distillation and the residue is recrystallized from water-ethanol. By the above procedure is obtained 0.8 g of the captioned compound as pale-white platelets. melting point: 194°-197° C.

Workup

  1. filtrationafter which the insolubles are filtered off
  2. concentrationThe filtrate is concentrated to dryness
  3. dissolutionthe concentrate is dissolved in chloroform
  4. filtrationAfter the insolubles are filtered off
  5. customthe chloroform is removed by distillation
  6. customthe residue is recrystallized from water-ethanol

Sources & evidence

ORD record
ord-8b75c21ec81841d3bbd7d8f22f4a0bed
Source dataset
uspto-grants-1978_12
Patent number
US04129654

Reaction notes

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