Lithium iodide → HCID 69976464, compound

HRID 581889Notes

Reaction equation

HRID 581889 reaction equation
C(=O)(O)[O-].[Na+].[I-].[Li+].[CH2:8]([C:10]1[C:11](=[O:27])[NH:12][C:13](=[O:26])[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].C1(C)C(S(O[CH2:38][CH2:39][CH:40]2[CH2:44][CH2:43][CH2:42][CH2:41]2)(=O)=O)=CC=CC=1>CN(C)C=O>[CH2:41]1[CH2:42][CH2:43][CH2:44][CH:40]1[CH:39]([N:14]1[C:15]([C:16](=[O:25])[C:17]2[CH:18]=[C:19]([CH3:24])[CH:20]=[C:21]([CH3:23])[CH:22]=2)=[C:10]([CH2:8][CH3:9])[C:11](=[O:27])[NH:12][C:13]1=[O:26])[CH3:38]

Participants

6

Reactant 4

HCID 66321Lithium iodideHCID 516892Sodium BicarbonateHCID 222565796-(3,5-dimethylbenzoyl)-5-ethylpyrimidine-2,4(1H,3H)-dioneHCID 86754222HCID 86754222, compound

Product 1

HCID 69976464HCID 69976464, compoundYield 24.5%

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-(cyclopentyl)ethyl toluenesulfonate (0.27 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 white solid (90 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-9b5319a6902f4510aa054f4245b7aca6
Source dataset
uspto-grants-1999_07
Patent number
US05922727

Reaction notes

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