Water → 9-Pivaloyloxymethyl-3,7-dimethyluric acid

HRID 1835698Notes

Reaction equation

HRID 1835698 reaction equation
[CH3:1][N:2]1[C:10]2[NH:9][C:8](=[O:11])[N:7]([CH3:12])[C:6]=2[C:5](=[O:13])[NH:4][C:3]1=[O:14].[H-].[Na+].[C:17]([O:23][CH2:24]Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19].O>CS(C)=O>[C:17]([O:23][CH2:24][N:9]1[C:8](=[O:11])[N:7]([CH3:12])[C:6]2[C:5](=[O:13])[NH:4][C:3](=[O:14])[N:2]([CH3:1])[C:10]1=2)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 831263,7-Dimethyluric AcidHCID 87885Chloromethyl pivalate

Product 1

HCID 224990389-Pivaloyloxymethyl-3,7-dimethyluric acidYield 28.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirring solution of 3,7-dimethyluric acid (0.40 g, 2.04 mmol) in dimethylsulfoxide (20 ml) was added sodium hydride (49 mg, 2.04 mmol) in one portion. After stirring for 45 minutes, a solution of chloromethyl pivalate (0.29 g, 2.04 mmol) in dimethylsulfoxide (1 ml). After stirring for 24 hours, water (50 ml) was added. After cooling to room temperature, the solid was filtered, rinsed with water (4×20 ml), with ether (20 ml) and dried under vacuum to give 9-pivaloyloxymethyl-3,7-dimethyluric acid (0.18 g, 28% yield) as a white solid.

Workup

  1. stirringAfter stirring for 24 hours
  2. filtrationthe solid was filtered
  3. washrinsed with water (4×20 ml), with ether (20 ml)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-2b197daa75e74cb0851c5293f5d97ccc
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

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