Pivaloyl chloride → HCID 9859583, compound

HRID 1884548Notes

Reaction equation

HRID 1884548 reaction equation
[CH3:1][N:2]1[C:9](=[O:10])[CH2:8][C:6](=[O:7])[N:5]([CH3:11])[C:3]1=[O:4].[C:12](Cl)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:12]([CH:8]1[C:9](=[O:10])[N:2]([CH3:1])[C:3](=[O:4])[N:5]([CH3:11])[C:6]1=[O:7])(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 69860Dimethylbarbituric acid

Product 1

HCID 9859583HCID 9859583, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 1,3-dimethylbarbituric acid (5 g, 32.02 mmol), 4-dimethylaminopyridine (4.69 g, 38.42 mmol) in dry CH2Cl2 (75 ml) was cooled to 0° C. and pivaloyl chloride (4.24 g, 35.22 mmol) added dropwise in 15 min. The reaction mixture was stirred at room temperature overnight, diluted with CH2Cl2 (150 ml) and washed with 2 N HCl solution (40 ml). The organic phase was dried over MgSO4 and evaporated. The residue was purified by chromatography using hexane/EtOAc/AcOH 15:5:0.1 as the mobile phase to give 5-pivaloyl-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione 11 (5.46 g, 71%).

Workup

  1. washwashed with 2 N HCl solution (40 ml)
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-330012fbf3e84a4fac4283d4bb6a2852
Source dataset
uspto-grants-2004_07
Patent number
US06765089B1

Reaction notes

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