2-TRIFLUOROMETHYL-PYRIMIDINE-5-CARBALDEHYDE Chemical Properties

Boiling point:

153℃

Density 

1.454

Flash point:

47℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-3.47±0.22(Predicted)

Appearance

White to light yellow Solid

InChI

InChI=1S/C6H3F3N2O/c7-6(8,9)5-10-1-4(3-12)2-11-5/h1-3H

InChIKey

GAUDQBASERVUGM-UHFFFAOYSA-N

SMILES

C1(C(F)(F)F)=NC=C(C=O)C=N1

2-TRIFLUOROMETHYL-PYRIMIDINE-5-CARBALDEHYDE Usage And Synthesis

Synthesis

Step B: Synthesis of 2-(trifluoromethyl)pyrimidine-5-carbaldehyde To a solution of ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate (25.5 g, 116.0 mmol) in dichloromethane (580 mL) was slowly added diisobutylaluminum hydride (1.0 M, 130.0 mL, 130.0 mmol) at -78 °C. The reaction mixture was kept stirred at -78 °C for 2 hours. Subsequently, the reaction was quenched by slow addition of hydrochloric acid (2.0 M). The mixture was gradually warmed up to ambient temperature. The mixture was extracted with ether (3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated to give the target product 2-(trifluoromethyl)pyrimidine-5-carbaldehyde (28.2 g).

References

[1] Patent: US2004/167142, 2004, A1. Location in patent: Page/Page column 23;24
[2] Patent: TW2016/5858, 2016, A. Location in patent: Page/Page column 133; 134
[3] Patent: US2014/107335, 2014, A1. Location in patent: Paragraph 0091; 0092
[4] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 1, p. 51 - 55
[5] Patent: WO2010/111058, 2010, A1. Location in patent: Page/Page column 69

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