ETHYL 2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE Chemical Properties

Melting point:

65 °C

Boiling point:

194℃

Density 

1.344

Flash point:

71℃

storage temp. 

under inert gas (nitrogen or Argon) at 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

Safety Information

HS Code 

2933599590

ETHYL 2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE Usage And Synthesis

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

ETHYL 2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE(304693-64-9)Related Product Information

• Ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate
• ETHYL 4-HYDROXY-2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
• 2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLIC ACID
• 5-Pyrimidinecarboxylic acid
• ETHYL 4-AMINO-2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
• ETHYL-2-TRIFLUOROMETHYL-4-METHYL-5-PYRIMIDINE CARBOXYLATE
• ETHYL-2-TRIFLUOROMETHYL-4-TRIFLUOROMETHYL-5-PYRIMIDINE CARBOXYLATE
• ETHYL-2-TRIFLUOROMETHYL-4-CYCLOPROPYL-5-PYRIMIDINE CARBOXYLATE
• ETHYL-2-TRIFLUOROMETHYL-4-(2-METHOXYPHENYL)-5-PYRIMIDINE CARBOXYLATE
• ETHYL-2-TRIFLUOROMETHYL-4-(2-CHLOROPHENYL)-5-PYRIMIDINE CARBOXYLATE
• ETHYL-2-TRIFLUOROMETHYL-4-(2-BROMOPHENYL)-5-PYRIMIDINE CARBOXYLATE
• ETHYL-2-TRIFLUOROMETHYL-4-(2-NITROPHENYL)-5-PYRIMIDINE CARBOXYLATE
• ETHYL-2-TRIFLUOROMETHYL-4-(2-FLUOROPHENYL)-5-PYRIMIDINE CARBOXYLATE
• ETHYL-2-TRIFLUOROMETHYL-4-PROPYL-5-PYRIMIDINE CARBOXYLATE
• ETHYL-2-TRIFLUOROMETHYL-4-(2-METHYLPHENYL)-5-PYRIMIDINE CARBOXYLATE
• ETHYL-2-TRIFLUOROMETHYL-4-ETHYL-5-PYRIMIDINE CARBOXYLATE
• ETHYL-2-TRIFLUOROMETHYL-4-ISOPROPYL-5-PYRIMIDINE CARBOXYLATE
• ETHYL 4-HYDRAZINO-2-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE