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 58504449 | HCID 58504449 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 58504394 | HCID 58504394 | 80.1% |
Reaction Steps
To a mixture of 6-chloro-N4-methyl-N4-[(1R)-1-methyl-2-phenylethyl]-2,4-pyrimidinediamine (0.4 g, 1.45 mmol), 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (0.46 g, 1.88 mmol) and Na2CO3 (0.38 g, 3.63 mmol) in 1,4-dioxane (6 mL) and water (3 mL) was added Pd(PPh3)4 (16 mg, 0.015 mmol), the reaction mixture was heated at 140° C. under microwave conditions with stirring for 40 minutes. The mixture was filtered and concentrated, and the resulting residue was purified by reverse phase chromatography using CH3CN in water from 45% to 55% (0.5% ammonium hydrogen carbonate in water) to afford the title compound (0.42 g) as a yellow solid. LC-MS (ES) m/z=362 [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-585432939fd3483ead599e2eb13f9df1 |
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| Source note | uspto-grants-2014_04 |
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