Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Phenacyl bromide | HCID 6259 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 57886945 | HCID 57886945 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57789974 | HCID 57789974 | 84.3% |
Reaction Steps
A solution of methyl 6-{(3R)-3-[(tertbutoxycarbonyl)amino]piperidin-1-yl}-5-(2-chloro-5-fluorobenzyl)-1-methyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidine-7-carboxylate (50 mg), α-bromoacetophenone (27 mg) and potassium carbonate (25 mg) in N,N-dimethylformamide was stirred at 25° C. for 14 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a preparative thin-layer chromatography (hexane/ethyl acetate=2/1) to obtain the title compound (51 mg) as a white solid.
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-2604c4d2109c4c6f9619ab1ee9a1dc2b |
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| Source note | uspto-grants-2009_10 |
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