2-(Trifluoromethyl)pyrimidine-5-carboxylic acid Chemical Properties

Melting point:

170-175℃

Boiling point:

220.7±40.0 °C(Predicted)

Density 

1.575±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

powder

pka

2.23±0.10(Predicted)

color 

Pale yellow

Water Solubility 

Slightly soluble in water.

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-60-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29335990

2-(Trifluoromethyl)pyrimidine-5-carboxylic acid Usage And Synthesis

Chemical Properties

White to pale yellow solid

Uses

2-(Trifluoromethyl)pyrimidine-5-carboxylic acid is used as pharmaceutical intermediate.

Synthesis

General procedure for the synthesis of 2-(trifluoromethyl)pyrimidine-5-carboxylic acid from ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate: To a 1 M aqueous lithium hydroxide solution (380 mL, 379.3 mmol) was added a solution of ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate (56.8 g, 252.8 mmol) dissolved in tetrahydrofuran (THF, 500 mL). The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, it was concentrated under vacuum to remove the organic solvent. The remaining aqueous solution was acidified with concentrated hydrochloric acid to pH 1. The resulting precipitate was collected by vacuum filtration to afford 44.4 g (91% yield) of 2-trifluoromethylpyrimidine-5-carboxylic acid as an off-white powder. The product was confirmed by 1H NMR (500 MHz, DMSO-d6): δ 9.44 (s, 2H). retention time (Rt) = 0.81 min by LCMS (Analytical Method A), and mass spectra (ESI negative ion mode): m/z = 190.9 ([M-H]-).

References

[1] Patent: WO2016/91776, 2016, A1. Location in patent: Page/Page column 362; 363
[2] Journal of medicinal chemistry, 2000, vol. 43, # 21, p. 3995 - 4004
[3] Patent: US2009/131431, 2009, A1. Location in patent: Page/Page column 148
[4] Patent: WO2007/36733, 2007, A1. Location in patent: Page/Page column 223

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