Lithium Hydroxide → {6-Oxo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6,7-dihydro-1H-purin-2-ylamino}-acetic acid

HRID 536024Notes

Reaction equation

HRID 536024 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][NH:6][C:7]1[N:8]([CH2:33][CH2:34][CH3:35])[C:9](=[O:32])[C:10]2[NH:11][C:12]([C:16]3[CH:17]=[N:18][N:19]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=4)[CH:20]=3)=[N:13][C:14]=2[N:15]=1)C.[OH-].[Li+]>C1COCC1.CO.O>[O:32]=[C:9]1[N:8]([CH2:33][CH2:34][CH3:35])[C:7]([NH:6][CH2:5][C:4]([OH:36])=[O:3])=[N:15][C:14]2[N:13]=[C:12]([C:16]3[CH:17]=[N:18][N:19]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=4)[CH:20]=3)[NH:11][C:10]1=2

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 67135287{6-Oxo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6,7-dihydro-1H-purin-2-ylamino}-acetic acid ethyl ester

Product 1

HCID 67134944{6-Oxo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6,7-dihydro-1H-purin-2-ylamino}-acetic acidYield 46%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of {6-Oxo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6,7-dihydro-1H-purin-2-ylamino}-acetic acid ethyl ester in THF (2 ml), MeOH (1 ml) and Water (1 ml) was added lithium hydroxide (0.02 g, 0.476 mmol) at 0° C. The reaction mixture was stirred at room temperature for overnight. The reaction mixture was concentrated and water was added. It was extracted with ethyl acetate. Ethyl acetate layer was washed with water and brine. Ethyl acetate layer was dried over sodium sulphate, filtered and concentrated under reduced pressure and the residue obtained was purified by column chromatography to obtain {6-Oxo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6,7-dihydro-1H-purin-2-ylamino}-acetic acid (0.035 g, 46%) as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added
  3. extractionIt was extracted with ethyl acetate
  4. washEthyl acetate layer was washed with water and brine
  5. dry with materialEthyl acetate layer was dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customthe residue obtained
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-b1033486d50f4ca3959e9707084c88f3
Source dataset
uspto-grants-2014_10
Patent number
US08859566B2

Reaction notes

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