Tetrabutylammonium Fluoride → 5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:19][C:20]1[CH:21]=[C:22]([C:26]2[N:27](COCC[Si](C)(C)C)[CH:28]=[C:29]3[C:34]=2[C:33](=[O:35])[N:32]([CH3:36])[C:31](=[O:37])[N:30]3[CH3:38])[CH:23]=[CH:24][CH:25]=1>C1COCC1>[F:19][C:20]1[CH:21]=[C:22]([C:26]2[NH:27][CH:28]=[C:29]3[C:34]=2[C:33](=[O:35])[N:32]([CH3:36])[C:31](=[O:37])[N:30]3[CH3:38])[CH:23]=[CH:24][CH:25]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Tetra-n-butylammonium fluoride solution (1.0M, 24.8 mL, 24.8 mmol) was added to a suspension of 5-(3-fluorophenyl)-1,3-dimethyl-6-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (1.00 g, 2.48 mmol) in THF (7 mL), and the mixture was stirred at 60° C. for 2 hours, then cooled to room temperature and stirred for 4 hours. The mixture was concentrated under vacuum and the residue was dissolved in ethyl acetate (50 mL). The mixture was washed with water (3×25 mL) and brine (1×25 mL). The organic phase was dried over magnesium sulfate and the solvent was evaporated under vacuum to afford the title compound.
Workup
- temperaturecooled to room temperature
- stirringstirred for 4 hours
- concentrationThe mixture was concentrated under vacuum
- dissolutionthe residue was dissolved in ethyl acetate (50 mL)
- washThe mixture was washed with water (3×25 mL) and brine (1×25 mL)
- dry with materialThe organic phase was dried over magnesium sulfate
- customthe solvent was evaporated under vacuum
Sources & evidence
- ORD record
- ord-99aea9858ce24ffe828e1b95f0542584
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09303035B2
Reaction notes
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