Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Trimethylsilyldiazomethane | HCID 167693 | — |
| Reactant | 4-(Trifluoromethyl)pyrimidine-2-carboxylic acid | HCID 25324146 | — |
| Catalyst | Acetic Acid | HCID 176 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 11579342 | HCID 11579342 | — |
Reaction Steps
4-(trifluoromethyl)pyrimidine-2-carboxylic acid (500 mg, 2.6 mmol) was dissolved in a mixture of 1 mL of THF and 300 μL of MeOH and cooled to 0° C. Trimethylsilyldiazomethane (2M in ether, 2.6 mL, 5.2 mmol) was added dropwise. The solution was stirred for 2 hours at 0° C., then 1 hour at rt. A few drops of AcOH were added, followed by water. The aqueous solution was extracted three times with EtOAc. The combined organic layers were dried (Na2SO4), filtered, and concentrated to give an oil which was used without further purification. MS (ESI): mass calcd. for C7H5F3N2O2, 206.0; m/z found, 207.0 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 9.24 (d, J=5.0 Hz, 1H), 7.87 (d, J=5.0 Hz, 1H), 4.10 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09040534B2 |
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| Source dataset | uspto-grants-2015_05 |
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| ORD ID | ord-2ecd3e9a2eb5413a89c3927d256f4a34 |
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| Source note | uspto-grants-2015_05 |
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