Ethyl Bromide → HCID 474609, compound

HRID 581884Notes

Reaction equation

HRID 581884 reaction equation
[C:1](=[O:4])(O)[O-].[Na+].[I-].[Li+].[CH2:8]([C:10]1[C:11](=[O:27])[NH:12][C:13](=O)[NH:14][C:15]=1[C:16](=[O:25])[C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=1)[CH3:9].[CH2:28](Br)[CH3:29]>CN(C)C=O>[CH:28]1([CH2:29][CH2:13][N:14]2[C:15]([C:16](=[O:25])[C:17]3[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=3)=[C:10]([CH2:8][CH3:9])[C:11](=[O:27])[NH:12][C:1]2=[O:4])[CH2:15][CH2:10][CH:8]=[CH:9]1

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 66321Lithium iodideHCID 516892Sodium BicarbonateHCID 222565796-(3,5-dimethylbenzoyl)-5-ethylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 474609HCID 474609, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of sodium bicarbonate (0.10 g, 1.2 mmol) and lithium iodide (13 mg, 0.1 mmol) were added to dimethylformamide solution (10 ml) of 5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione (0.27 g, 1.0 mmol) and 2-(cyclopent-2-en-yl))ethyl bromide (0.18 g, 1.0 mmol). And then, the reaction mixture was stirred at 90° C. for overnight, concentrated for removement of dimethylformamide, extracted with dichloromethane, dried, filtered and separated by column chromatography to give a desirable product as a white solid (112 mg).

Workup

  1. concentrationconcentrated for removement of dimethylformamide
  2. extractionextracted with dichloromethane
  3. customdried
  4. filtrationfiltered
  5. customseparated by column chromatography

Sources & evidence

ORD record
ord-3f3d6d1d9f7c4cdfbc0ef5525bfa44e9
Source dataset
uspto-grants-1999_07
Patent number
US05922727

Reaction notes

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