Succinic anhydride → HCID 68984624, compound

HRID 28590Notes

Reaction equation

HRID 28590 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:26])=[C:6]([C:8]2[N:13]=[C:12]([NH2:14])[N:11]=[C:10]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH:9]=2)[CH:7]=1.[C:27]1(=O)[O:32][C:30](=[O:31])[CH2:29][CH2:28]1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:26])=[C:6]([C:8]2[CH:9]=[C:10]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:22]([F:23])([F:25])[F:24])=[CH:20][CH:21]=3)[N:11]=[C:12]([N:14]3[C:30](=[O:31])[CH2:29][CH2:28][C:27]3=[O:32])[N:13]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 100225822,4-Pyrimidinediamine, 6-(5-chloro-2-methylphenyl)-N4-(4-(trifluoromethyl)phenyl)-

Product 1

HCID 68984624HCID 68984624, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of the title compound of Example 29 (0.19 g, 0.50 mmol) and succinic anhydride (0.30 g, 3.0 mmol) in toluene (18 ml) was heated under reflux for 6 hours. After cooled to room temperature, the mixture was filtered. The filtrate was washed with saturated aqueous sodium bicarbonate solution (3×10 ml), dried over magnesium sulfate, and concentrated under reduced pressure to provide 1-[4-(5-chloro-2-methyl-phenyl)-6-(4-trifluoromethyl-phenylamino)-pyrimidin-2-yl]-pyrrolidine-2,5-dione as a white solid (96% yield).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. filtrationthe mixture was filtered
  4. washThe filtrate was washed with saturated aqueous sodium bicarbonate solution (3×10 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e872ee3d99d4058ab67ebbe21f27bf9
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

Loading…