Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Urea | HCID 1176 | — |
| Reactant | Ethyl 4,4,4-trifluoroacetoacetate | HCID 67793 | — |
| Reactant | Ethylorthoformate | HCID 53630039 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Product | HCID 178469855 | HCID 178469855 | 69% |
Reaction Steps
A mixture of ethyl 4,4,4-trifluoroacetoacetate (23.1 g), urea (7.54 g) and ethyl orthoformate (18.6 g) is stirred at 130° C. under argon gas atmosphere for 1.5 hours. To the reaction mixture is added xylene (100 mL) and the mixture is stirred at 140° C. for 17 hours. The reaction mixture is evaporated to remove solvent and the residue is diluted with methanol. The solution is treated with an activated carbon powder, concentrated in vacuo, and triturated in diisopropylether to give ethyl 2-hydroxy-4-trifluoromethyl-5-pyrimidinecarboxylate (20.3 g, yield; 69%) as crystals. MS (ESI) m/z; 235 [M−H]−
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07384952B2 |
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| Source dataset | uspto-grants-2008_06 |
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| ORD ID | ord-743c2e459c6f4e37beb7f7a6c2460152 |
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| Source note | uspto-grants-2008_06 |
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