Hydrogen Peroxide → HCID 178431782, compound

HRID 241002Notes

Reaction equation

HRID 241002 reaction equation
OO.[CH:3]([C:6]1[NH:11][C:10](=S)[NH:9][C:8](=[O:13])[C:7]=1[CH3:14])([CH3:5])[CH3:4].C(=O)([O-])[O-].[Na+].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O>[CH:3]([C:6]1[N:11]=[CH:10][N:9]=[C:8]([OH:13])[C:7]=1[CH3:14])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 12512044HCID 12512044, compound

Product 1

HCID 178431782HCID 178431782, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 30% hydrogen peroxide (12 mL) and water (23 mL) was slowly added 6-isopropyl-5-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (1.0 g, 5.4 mmol). The reaction mixture was stirred at 70° C. for 3 h. After cooling to room temperature, saturated sodium carbonate was slowly added until the pH reached 10. To this mixture was slowly added a 1 M solution of sodium thiosulfate until residual peroxide was quenched, whereupon the aqueous solution was concentrated to dryness. The residue was suspended in chloroform (100 mL), filtered to remove inorganic salts and the filtrate concentrated to provide 6-isopropyl-5-methylpyrimidin-4-ol (0.25 g, 30% yield) as a white solid that was used without further purification. MS (EI) for C8H12N2O: 153 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. customwas quenched, whereupon the aqueous solution
  3. concentrationwas concentrated to dryness
  4. filtrationfiltered
  5. customto remove inorganic salts
  6. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-0ca1d605bdbf4a15acb0c366a0bc203b
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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