Water → HCID 15544681, compound

HRID 650903Notes

Reaction equation

HRID 650903 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[NH:17][C:16]2=[O:26])=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH:12]([CH3:14])[CH3:13])[CH2:7]2.[C:27](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:27])[C:16]2=[O:26])=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH:12]([CH3:13])[CH3:14])[CH2:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21710142HCID 21710142, compound

Product 1

HCID 15544681HCID 15544681, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.90 gram (0.0023 mole) of 3-[7-chloro-2-(1-methylethyl)-isoindolin-1-on-4-yl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, 0.42 gram (0.0030 mole) of potassium carbonate, and 0.45 gram (0.0030 mole) of methyl iodide in 60 mL of DMF was stirred at 25 C. for about 18 hours. The reaction mixture was then poured into water and extracted with diethyl ether. The organic layer was dried with magnesium sulfate, filtered, and concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel using mixtures of methylene chloride and EtOAc as eluants. The fractions containing product were combined and concentrated under reduced pressure, yielding about 0.65 gram of subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure to a residue
  5. customThe residue was purified by column chromatography on silica gel using mixtures of methylene chloride and EtOAc as eluants
  6. additionThe fractions containing product
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee49c36cfc0f4a99b5515c7b6a7bba30
Source dataset
uspto-grants-2001_08
Patent number
US06277847B1

Reaction notes

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