Allyl bromide → HCID 22256583, compound

HRID 1611369Notes

Reaction equation

HRID 1611369 reaction equation
[CH2:1]([C:3]1[C:4](=[O:19])[NH:5][C:6](=[O:18])[NH:7][C:8]=1[O:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[CH:11]=1)[CH3:2].[CH2:20](Br)[CH:21]=[CH2:22].C(=O)(O)[O-].[Na+].[I-].[Li+]>CN(C)C=O>[CH2:22]([N:7]1[C:8]([O:9][C:10]2[CH:11]=[C:12]([CH3:17])[CH:13]=[C:14]([CH3:16])[CH:15]=2)=[C:3]([CH2:1][CH3:2])[C:4](=[O:19])[NH:5][C:6]1=[O:18])[CH:21]=[CH2:20]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 66321Lithium iodideHCID 516892Sodium BicarbonateHCID 109232665-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione

Product 1

HCID 22256583HCID 22256583, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione (258 mg, 1.0 mmol) and allyl bromide(121 mg, 1.0 mmol) dissolved in dimethylformamide(5 ml), sodium bicarbonate(126 mg, 1.50 mmol) and lithium iodide(13.0 mg, 0.10 mmol) were added and stirred at 90° C. for 24 hours. The resulting product was distilled under the reduced pressure to remove dimethylformamide and purified by column chromatography to obtain the titled compound as a white solid(157 mg, yield: 52.3%).

Workup

  1. distillationThe resulting product was distilled under the reduced pressure
  2. customto remove dimethylformamide
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-8563a7cdc08b473e956d959dbc127ebc
Source dataset
uspto-grants-2006_01
Patent number
US06987114B1

Reaction notes

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