Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile | HCID 51350951 | — |
| Reactant | HCID 178488780 | HCID 178488780 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 178488779 | HCID 178488779 | 55.3% |
Reaction Steps
A mixture of 4-chloro-6-(2-{4-[4-(methyloxy)phenyl]-1H-imidazol-2-yl}-4-morpholinyl)-2-pyrimidinamine (1.0 g, 2.59 mmol), 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (0.83 g, 3.36 mmol), Na2CO3 (0.685 g, 6.46 mmol) and Pd(PPh3)4 (0.30 g, 0.26 mmol) in 1,4-dioxane (8 mL) and water (2 mL) was heated at 140° C. under microwave conditions with stirring for 1 hour. The reaction mixture was filtered, washed by ethyl acetate (100 mL), and concentrated. The resulting residue was purified by silica gel chromatography using EtOAc/petroleum ether (3:1) to afford the title compound (675 mg) as a yellow solid. LC-MS (ES) m/z=472 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08697685B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-343b1ac8652d4f3bbbf510bad71d79d6 |
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| Source note | uspto-grants-2014_04 |
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