Water → HCID 86723876, compound

HRID 576772Notes

Reaction equation

HRID 576772 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]([C:14]2[N:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=3)[N:17]=[CH:16][CH:15]=2)=[C:10]([CH3:27])[N:9]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[C:8]1=[O:38])C.[OH-].[Na+].O>CO.C(OCC)C>[C:25]([C:22]1[CH:21]=[CH:20][C:19]([N:18]2[C:14]([C:11]3[C:12](=[O:13])[N:7]([CH2:6][CH2:5][C:4]([OH:39])=[O:3])[C:8](=[O:38])[N:9]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:36])([F:37])[F:35])[CH:29]=4)[C:10]=3[CH3:27])=[CH:15][CH:16]=[N:17]2)=[CH:24][CH:23]=1)#[N:26]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86723877HCID 86723877, compound

Product 1

HCID 86723876HCID 86723876, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3-[5-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-4-methyl-2,6-dioxo-3-(3-trifluoromethylphenyl)-2,3-dihydropyrimidin-1(6H)-yl]propanoic acid ethyl ester (prepared in Example 4) (351.0 mg) in methanol (1.0 ml) was cooled under ice-cooling and thereto was added 2N aqueous sodium hydroxide solution (340 μl) and the resulting mixture was stirred at room temperature for twelve hours. The reaction mixture was diluted with diethylether (30 ml) and thereto was added water (30 ml). The organic layer and the aqueous layer were separated and the aqueous layer was then acidified with sodium hydrogen sulfate (500 mg) and extracted with ethyl acetate (50 ml×3). The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained amorphous was washed with hexane (30 ml) to afford 3-[5-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-4-methyl-2,6-dioxo-3-(3-trifluoromethylphenyl)-2,3-dihydropyrimidin-1(6H)-yl]propanoic acid (239.5 mg).

Workup

  1. temperaturecooling
  2. customThe organic layer and the aqueous layer were separated
  3. extractionextracted with ethyl acetate (50 ml×3)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe obtained amorphous was washed with hexane (30 ml)

Sources & evidence

ORD record
ord-f3605ce6709b4a6caa8e85fa099f3535
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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