Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | Benzyl [4-(4-chloropyrimidin-6-yloxy)-2,5-difluorophenyl]carbamate | HCID 57470873 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57470875 | HCID 57470875 | 34.4% |
Reaction Steps
Benzyl [4-(4-chloropyrimidin-6-yloxy)-2,5-difluorophenyl]carbamate (1.96 g) was dissolved in N,N-dimethylformamide (20 ml). Sodium azide (650 mg) was added thereto, followed by stirring at 60° C. for 2 hr. The reaction mixture was allowed to cool to room temperature, then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate=3:1). Fractions containing the target compound were concentrated under reduced pressure and the residue was dried under reduced pressure to provide the titled compound as white crystals (685 mg, 34%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07855290B2 |
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| Source dataset | uspto-grants-2010_12 |
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| ORD ID | ord-5e39d9d59a20419789728863cbe94674 |
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| Source note | uspto-grants-2010_12 |
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