Water → 2-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetic acid

HRID 927217Notes

Reaction equation

HRID 927217 reaction equation
[OH-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[N:16]([CH2:17][C:18]([O:20]C)=[O:19])[C:15](=[O:22])[N:14]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[C:13]3[CH2:33][CH2:34][C:35](=[O:36])[C:12]2=3)=[CH:7][CH:6]=1)#[N:4].O>O1CCCC1>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[N:16]([CH2:17][C:18]([OH:20])=[O:19])[C:15](=[O:22])[N:14]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:30])[F:31])[CH:24]=3)[C:13]3[CH2:33][CH2:34][C:35](=[O:36])[C:12]2=3)=[CH:9][CH:10]=1)#[N:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 90310893Methyl 2-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetate

Product 1

HCID 903109622-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous sodium hydroxide solution (1 M, 15.0 mL, 15.0 mmol) is added to a solution of methyl 2-(4-(4-cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)acetate (example 3, 2.64 g, 5.62 mmol) in tetrahydrofuran (40 mL) and the mixture is stirred at room temperature for 4 h. Water is added and the mixture is extracted three times with ethyl acetate. The aqueous layer is acidified a) with hydrogen chloride and extracted twice with dichloromethane. These organic layers are combined and concentrated. Yield: 1.84 g; ESI mass spectrum [M+H]+=456; Retention time HPLC: 0.84 min (Z018_S04).

Workup

  1. extractionthe mixture is extracted three times with ethyl acetate
  2. extractionextracted twice with dichloromethane
  3. concentrationconcentrated
  4. custom0.84 min (Z018_S04)

Sources & evidence

ORD record
ord-38068efda92f4ec0ad1bee4e8cb324b7
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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