Water → HCID 86723531, compound

HRID 2201299Notes

Reaction equation

HRID 2201299 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][CH2:6][CH2:7][N:8]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:15]2[C:10]([N:11]([CH3:26])[C:12](=[O:25])[N:13]([CH3:24])[C:14]2=[O:23])=[CH:9]1)C.O.[OH-].[Li+]>C1COCC1>[CH3:26][N:11]1[C:10]2=[CH:9][N:8]([CH2:7][CH2:6][CH2:5][C:4]([OH:27])=[O:3])[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:15]2[C:14](=[O:23])[N:13]([CH3:24])[C:12]1=[O:25]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium Hydroxide2×HCID 86723530HCID 86723530, compound

Product 1

HCID 86723531HCID 86723531, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

4-(1,3-Dimethyl-2,4-dioxo-5-phenyl-1,2,3,4-tetrahydro-pyrrolo[3,4-d]pyrimidin-6-yl)-butyric acid ethyl ester (step 1)(1.01 g, 2.73 mmol) was dissolved in THF (10 ml) and water (10 ml) and lithium hydroxide (0.655 g, 27.3 mmol) were added. The mixture was stirred at 60° C. for 5 hours. Further lithium hydroxide (0.655 g, 27.3 mmol) was added and the mixture stirred at 60° C. for a further 24 hours. The reaction mixture was cooled to RT and concentrated under reduced pressure. The residue was acidified using 1M HCl(aq) and extracted with chloroform (5×). The combined organic phases were passed through a hydrophobic frit and evaporated under reduced pressure. The title product was obtained as a white solid.

Workup

  1. stirringthe mixture stirred at 60° C. for a further 24 hours
  2. temperatureThe reaction mixture was cooled to RT
  3. concentrationconcentrated under reduced pressure
  4. extractionextracted with chloroform (5×)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d8241902be9c4731a1edc890fd28e777
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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