Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(Trifluoromethyl)phenylboronic acid | HCID 2734389 | — |
| Reactant | 2-chloro-5-methyl-4-[[3-(trifluoromethyl)phenyl]methyl]pyrimidine | HCID 12056714 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 18628527 | HCID 18628527 | — |
Reaction Steps
The title compound of Example 1, Step A (0.6 g, 2 mmol), 4-trifluoromethyl-benzeneboronic acid (1.1 g, 6 mmol), and bis(triphenylphosphine)palladium dichloride were dissolved in dimethoxyethane (15 mL) and aqueous sodium carbonate (2 M, 4 mmol). The resulting mixture was heated at 80° C. for 3 h. The mixture was diluted with dichloromethane (50 mL) and water (50 mL). The dichloromethane layer was dried over magnesium sulfate, concentrated under reduced pressure, and the residue was subjected to silica gel chromatography using hexaneslethyl acetate (85:15). The title compound of Step A, a compound of the invention, was isolated as a white solid (0.56 g) melting at 159-161° C. 1H NMR (CDCl3/200 MHz) 2.47 (s, 3H), 7.62-7.78 (m, 3H), 7.94 (d, 1H), 8.17 (d, 1H), 8.34 (s, 1H), 8.5 (d, 2H), 8.9 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06525001B1 |
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| Source dataset | uspto-grants-2003_02 |
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| ORD ID | ord-de8bd4910d1a4b128fbe3759a0e7deae |
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| Source note | uspto-grants-2003_02 |
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