Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Trifluoroacetic anhydride | HCID 9845 | — |
| Reactant | HCID 86606998 | HCID 86606998 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 70323530 | HCID 70323530 | 69% |
Reaction Steps
To a stirred solution of tert-butyl (2-carbamoyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-6-yl)methylcarbamate (Example 58, Step 2, 30 mg, 0.07 mmol) in dioxane (1.5 mL) was added pyridine (10.5 mg, 0.13 mmol) and TFAA (15.4 mg, 0.07 mmol). The reaction was kept at room temperature for 16 and additional pyridine (10.5 mg, 0.13 mmol) and TFAA (15.4 mg, 0.07 mmol) were added. After 5 h, the reaction was quenched by H2O and diluted with EtOAc. The organic layer was washed with satd aq NH4Cl and brine prior to drying over MgSO4. Filtration, concentration under reduced pressure and purification by silica gel chromatography afforded tert-butyl (2-cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-6-yl)methylcarbamate (20 mg, 69% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07635699B2 |
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| Source dataset | uspto-grants-2009_12 |
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| ORD ID | ord-9eae1712bd8b4621b5378c6e179cc996 |
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| Source note | uspto-grants-2009_12 |
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