2,4-dichloro-6-(trifluoromethyl)pyrimidine Chemical Properties

Melting point:

-48--46 °C

Boiling point:

37-38 °C(Press: 0.7 Torr)

Density 

1.589

refractive index 

1.4640

storage temp. 

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

pka

-7.56±0.32(Predicted)

form 

Liquid

color 

Pale yellow

InChI

InChI=1S/C5HCl2F3N2/c6-3-1-2(5(8,9)10)11-4(7)12-3/h1H

InChIKey

ZTNFYAJHLPMNSN-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(C(F)(F)F)=CC(Cl)=N1

Safety Information

HS Code 

29335990

2,4-dichloro-6-(trifluoromethyl)pyrimidine Usage And Synthesis

Uses

2,4-Dichloro-6-trifluoromethylpyrimidine is a useful synthetic intermediate. It can be used to synthesize 2,4-diaminopyrimidines derivatives that show antiplasmodial activities.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 24, p. 1243, 1987 DOI: 10.1002/jhet.5570240502

Synthesis

Synthesis of 2,4-dichloro-6-trifluoromethylpyrimidine (XXVII): 6-(trifluoromethyl)uracil (XXVI) (10.0 g, 55 mmol) was dissolved in anhydrous acetonitrile (50 mL) under dry conditions. Subsequently, N,N-dimethylaniline (6.5 mL, 51 mmol) and phosphorus oxychloride (POCl3) (19 mL, 204 mmol) were added sequentially to the reaction system. Almost complete dissolution of the solids was observed, forming a dark colored solution. The reaction mixture was heated to reflux and the reflux reaction was maintained for 6 hours. Upon completion of the reaction, the heating was stopped and the volatile components were removed under reduced pressure. The residue was dissolved in ether (Et2O) (300 mL), the resulting ether solution was washed sequentially with deionized water (2 x 200 mL), dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated to give 2,4-dichloro-6-trifluoromethylpyrimidine (XXVII) as a yellow oil (11.3 g, 94% yield). The product was characterized by 1H NMR (CDCl3): δ 7.7 (s, 1H); GC/MS analysis showed m/z (relative abundance) 220 (12), 218 (67), 216 (100).

References

[1] Patent: US2009/93480, 2009, A1. Location in patent: Page/Page column 6-7
[2] Patent: WO2016/42452, 2016, A1. Location in patent: Page/Page column 114; 115
[3] Patent: WO2016/42453, 2016, A1. Location in patent: Page/Page column 51
[4] European Journal of Organic Chemistry, 2006, # 6, p. 1593 - 1598
[5] Patent: WO2015/191630, 2015, A1. Location in patent: Paragraph 00398

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