Oxygen → SJ-3366

HRID 650674Notes

Reaction equation

HRID 650674 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].[CH:24]1([CH2:29]Br)[CH2:28][CH:27]=[CH:26][CH2:25]1.[O:31]=O>CN(C)C=O.O>[CH:24]1([CH2:29][N:9]2[C:10]([C:11](=[O:31])[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])[CH2:28][CH:27]=[CH:26][CH2:25]1

Participants

7

Reactant 4

HCID 977OxygenHCID 24758Sodium hydrideHCID 98822335-Ethyl-6-(alpha-cyano-3,5-dimethylbenzyl)-2,4-pyrimidinedioneHCID 112174134-(Bromomethyl)cyclopent-1-ene

Product 1

HCID 474597SJ-3366Yield 65.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

48 mg of 60% sodium hydride (1.20 mmol) was slowly added to 0.28 g of 5-ethyl-6-(α-cyano-3,5-dimethylbenzyl)-2,4-pyrimidinedione (1.0 mmol) dissolved in 10 ml of dimethyl formamide, and the mixture was stirred at room temperature for one hour. Then, 0.32 g of (cyclopent-3-en-1-yl)methyl bromide (2.0 mmol) was added to the resulting mixture and stirred at the temperature of 50˜60° C. for 48 hours with injection of oxygen. After cooling, 20 ml of distilled water was added to the resulting product, and extracted with 20 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 0.23 g of the titled compound as a white solid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with 20 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-5da5ca29f3ff4c5db22c3f1cbf23dcf8
Source dataset
uspto-grants-2001_08
Patent number
US06274732B1

Reaction notes

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