Water → HCID 86723537, compound

HRID 2201306Notes

Reaction equation

HRID 2201306 reaction equation
[OH-].[Li+].[CH3:3][N:4]1[C:9]2=[CH:10][N:11]([CH2:20][CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])[C:12]([C:13]3[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=3)=[C:8]2[C:7](=[O:28])[N:6]([CH3:29])[C:5]1=[O:30].O>C1COCC1>[CH3:3][N:4]1[C:9]2=[CH:10][N:11]([CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:12]([C:13]3[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=3)=[C:8]2[C:7](=[O:28])[N:6]([CH3:29])[C:5]1=[O:30]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 86723538HCID 86723538, compound

Product 1

HCID 86723537HCID 86723537, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (2.64 g, 63.0 mmol) was added to a solution of ethyl 4-(1,3-dimethyl-2,4-dioxo-5-m-tolyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)butanoate (step 1) (4.83 g, 12.6 mmol) in THF (48 mL)/water (12 mL). The mixture was stirred at room temperature for 24 hours. The organic solvent was largely removed under vacuum, the residue was acidified to pH 1, using 1M. The precipitate was extracted into chloroform (1×100 mL, 4×50 mL). The combined organic extracts were dried with magnesium sulfate and the solvent was removed under vacuum. The resulting solid was dried under vacuum at 50° C. to give the title compound.

Workup

  1. customThe organic solvent was largely removed under vacuum
  2. extractionThe precipitate was extracted into chloroform (1×100 mL, 4×50 mL)
  3. dry with materialThe combined organic extracts were dried with magnesium sulfate
  4. customthe solvent was removed under vacuum
  5. customThe resulting solid was dried under vacuum at 50° C.

Sources & evidence

ORD record
ord-89344399739c4bef9cacd116fc3035ad
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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