Water → 3-(1,3-Dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propanoic acid

HRID 2201195Notes

Reaction equation

HRID 2201195 reaction equation
[CH3:1][N:2]1[C:7]2=[CH:8][N:9]([CH2:17][CH2:18][C:19]([O:21]C)=[O:20])[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:6]2[C:5](=[O:23])[N:4]([CH3:24])[C:3]1=[O:25].O.[Li+].[OH-]>C1COCC1.CCOC(C)=O>[CH3:1][N:2]1[C:7]2=[CH:8][N:9]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:6]2[C:5](=[O:23])[N:4]([CH3:24])[C:3]1=[O:25]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 86723437Methyl 3-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propanoate

Product 1

HCID 867234383-(1,3-Dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propanoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 3-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propanoate (step 2) (3.24 g, 9.49 mmol) in THF (33.9 mL)/water (33.9 mL) and LiOH (2.273 g, 95 mmol) was heated to 50° C. for 1 hr. The reaction mixture was diluted with EtOAc (50 ml) and the layers separated. The organics were then washed with water (3×50 ml). The aqueous extracts were combined and the pH adjusted to approx. pH3 with 5M HCl. The resulting precipitate was isolated using suction filtration.

Workup

  1. customthe layers separated
  2. washThe organics were then washed with water (3×50 ml)
  3. customThe resulting precipitate was isolated
  4. filtrationsuction filtration

Sources & evidence

ORD record
ord-f0a4ce6291904c429b235ee0a21d41f1
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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