Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrogen Peroxide | HCID 784 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Sodium Sulfite | HCID 24437 | — |
| Reactant | tert-Butyl {(3R)-1-[5-(2-chloro-5-fluorobenzyl)-2,7-dicyano-3-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate | HCID 86625682 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 57887016 | HCID 57887016 | 46% |
Reaction Steps
Potassium carbonate (42 mg) and then an aqueous hydrogen peroxide solution (a 30-35% aqueous solution, 170 μl) were added dropwise to a solution of tert-butyl {(3R)-1-[5-(2-chloro-5-fluorobenzyl)-2,7-dicyano-3-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate (162 mg) in a mixture of dimethyl sulfoxide (10 ml) and water (2 ml), and the resulting mixture was stirred overnight at room temperature. A 10% aqueous sodium sulfite solution was added to the reaction solution, followed by extraction with ethyl acetate (200 ml). The organic layer was washed with a 10% aqueous potassium carbonate solution and a saturated aqueous sodium chloride solution, dried over sodium sulfate and then filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain the title compound (77 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07601728B2 |
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| Source dataset | uspto-grants-2009_10 |
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| ORD ID | ord-b7c49624145e450d97786597f68a891d |
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| Source note | uspto-grants-2009_10 |
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