Water → HCID 117840271, compound

HRID 714802Notes

Reaction equation

HRID 714802 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][C:6]1([CH2:25][CH3:26])[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]3[CH:19]=[N:20][N:21]([CH3:23])[CH:22]=3)[N:12]=2)[C:7]1=[O:24])C.[OH-].[Na+].O>C(O)C>[CH2:25]([C:6]1([CH2:5][C:4]([OH:27])=[O:3])[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]3[CH:19]=[N:20][N:21]([CH3:23])[CH:22]=3)[N:12]=2)[C:7]1=[O:24])[CH3:26]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 131734073HCID 131734073, compound

Product 1

HCID 117840271HCID 117840271, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl(3-ethyl-1-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-2-oxopyrrolidin-3-yl)acetate (270 mg) obtained in Step E in ethanol (5 mL) was added dropwise 2M aqueous sodium hydroxide solution (1.4 mL), and the mixture was stirred overnight at room temperature. To the reaction mixture was added water, and the mixture was washed with diethyl ether. The aqueous layer was neutralized with 2M hydrochloric acid, and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized (ethyl acetate) to give the title compound (100 mg).

Workup

  1. washthe mixture was washed with diethyl ether
  2. extractionextracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was recrystallized (ethyl acetate)

Sources & evidence

ORD record
ord-cd34bd6d18de4bfa86bceb6e83cad289
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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