Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Bromophenol | HCID 7244 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine | HCID 16747837 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 21865142 | HCID 21865142 | 81.2% |
Reaction Steps
To a solution of 2-bromophenol (2.595 g, 15 mmol, Aldrich) in anhydrous DMF (20 mL) was added NaH (0.68 g, 17 mmol, 60% suspension in mineral oil, Aldrich) in small portions with stirring at room temperature. The reaction mixture was stirred for 0.5 h at room temperature and 4-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine, (Example 2(a), Method A), (2.586 g, 10 mmol) was added in one portion. The reaction mixture was stirred for 18 h at room temperature and most of the solvent was removed in vacuo. The residue was dissolved in EtOAc, washed with 1N NaOH (2×) and H2O, dried over Na2SO4, filtered and concentrated in vacuum. The residue was recrystallized from EtOAc/hexane to give 3.21 g (81%) of the title compound. MS (ESI, pos. ion) m/z: 397 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07144888B2 |
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| Source dataset | uspto-grants-2006_12 |
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| ORD ID | ord-d7301dc0b7b24273af917cd9da02abc7 |
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| Source note | uspto-grants-2006_12 |
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