| Identification | Back Directory | [Name]
ETHYL 2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE | [CAS]
304693-64-9 | [Synonyms]
Ethyl 2-(trifluoromethyl)
5-(Ethoxycarbonyl)-2-(trifluoromethyl)pyrimidine
ETHYL 2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
5-PYRIMIDINECARBOXYLIC ACID, 2-(TRIFLUOROMETHYL)-, ETHYL ESTER
ETHYL 2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE ISO 9001：2015 REACH | [Molecular Formula]
C8H7F3N2O2 | [MDL Number]
MFCD09754048 | [MOL File]
304693-64-9.mol | [Molecular Weight]
220.149 |
| Chemical Properties | Back Directory | [Melting point ]
65 °C | [Boiling point ]
194℃ | [density ]
1.344 | [Fp ]
71℃ | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
powder | [pka]
-3.50±0.22(Predicted) | [color ]
Yellow | [InChI]
InChI=1S/C8H7F3N2O2/c1-2-15-6(14)5-3-12-7(13-4-5)8(9,10)11/h3-4H,2H2,1H3 | [InChIKey]
LRUCUGOOQHJEQP-UHFFFAOYSA-N | [SMILES]
C1(C(F)(F)F)=NC=C(C(OCC)=O)C=N1 |
| Hazard Information | Back Directory | [Uses]
Ethyl 2-(Trifluoromethyl)pyrimidine-5-carboxylate is used to prepare NF-κB and AP-1 gene inhibitors. | [Synthesis]
Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate (55.7 g) was added to a mixture of 10% palladium-carbon catalyst (0.3 g), ethanol (1000 ml) and N,N-diisopropylethylamine (90 ml) as a starting material. The reaction was shaken under hydrogen atmosphere at 1 atm for 2 hours. After completion of the reaction, the catalyst was removed by filtration and the solvent was removed by evaporation. The residue was dissolved in dichloromethane, washed sequentially with ammonium chloride solution and water, dried over anhydrous magnesium sulfate, and the solvent was evaporated to afford the target product, ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate, as a light yellow solid (48 g, 100% yield). The structure of the product was confirmed by 1H-NMR (CDCl3) δ 9.42 (2H, s), 4.51 (2H, q), 1.45 (3H, t) and 13C-NMR (CDCl3) δ 162.7,159.4 (2C), 159.3 (q, J=37Hz), 126.3,119.6 (q, J=275Hz), 62.9,. 14.4 Confirmed. | [References]
[1] Patent: US2004/167142, 2004, A1. Location in patent: Page/Page column 23
[2] Patent: US2013/72470, 2013, A1. Location in patent: Paragraph 0389-0391
[3] Patent: WO2016/91776, 2016, A1. Location in patent: Page/Page column 362
[4] Patent: TW2016/5858, 2016, A. Location in patent: Page/Page column 134
[5] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 1, p. 51 - 55 |
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