Oxygen → SJ-3366

HRID 650675Notes

Reaction equation

HRID 650675 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[C:6](=[O:23])[NH:7][C:8](=[O:22])[NH:9][C:10]=1[CH:11](C#N)[C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=1)[CH3:4].C1(C)C=CC(S(O[CH2:34][CH:35]2[CH2:39][CH:38]=[CH:37][CH2:36]2)(=O)=O)=CC=1.[O:41]=O>CN(C)C=O.O>[CH:35]1([CH2:34][N:9]2[C:10]([C:11](=[O:41])[C:12]3[CH:13]=[C:14]([CH3:19])[CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:5]([CH2:3][CH3:4])[C:6](=[O:23])[NH:7][C:8]2=[O:22])[CH2:39][CH:38]=[CH:37][CH2:36]1

Participants

7

Reactant 4

HCID 977OxygenHCID 24758Sodium hydrideHCID 98822335-Ethyl-6-(alpha-cyano-3,5-dimethylbenzyl)-2,4-pyrimidinedioneHCID 12930331(Cyclopent-3-en-1-yl)methyl para-toluenesulfonate

Product 1

HCID 474597SJ-3366Yield 71.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

480 mg of 60% sodium hydride (12.0 mmol) was slowly added to 2.83 g of 5-ethyl-6-(α-cyano-3,5-dimethylbenzyl)-2,4-pyrimidinedione (10.0 mmol) dissolved in 50 ml of dimethyl formamide, and the mixture was stirred at room temperature for one hour. Then, to the resulting solution, 5.07 g of (cyclopent-3-en-1-yl)methyl para-toluenesulfonate (20.0 mmol) was added and stirred with injecting oxygen at 50˜60° C. for 48 hours. After cooling, 200 ml of distilled water was added to the resulting product, and extracted with 200 ml of ethyl acetate (2 ×). The obtained extract was dried with anhydrous magnesium sulfate and concentrated under the reduced pressure. Then, the concentrated residue was separated and purified with column chromatography (hexane:ethyl acetate=2:1) to obtain 2.52 g of the titled compound as a white solid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with 200 ml of ethyl acetate (2 ×)
  3. extractionThe obtained extract
  4. dry with materialwas dried with anhydrous magnesium sulfate
  5. concentrationconcentrated under the reduced pressure
  6. customThen, the concentrated residue was separated
  7. custompurified with column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-d426185e86a547a5adfb7b065ab74667
Source dataset
uspto-grants-2001_08
Patent number
US06274732B1

Reaction notes

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