Ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate Chemical Properties

Melting point:

36 °C

Boiling point:

95 °C

Density 

1.45g/ml

storage temp. 

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

form 

low-melting solid

pka

-4.91±0.29(Predicted)

color 

Yellow

CAS DataBase Reference

720-01-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37/39

Hazard Note 

Irritant

HS Code 

29335990

Ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate Usage And Synthesis

Uses

Ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate is used as a pharmaceutical intermediate in pharmaceutical synthesis and scientific research.

Synthesis

General procedure for the synthesis of ethyl 2-trifluoromethyl-4-chloropyrimidine-5-carboxylate using ethyl 4-hydroxy-2-trifluoromethylpyrimidine-5-carboxylate as starting material: 1. ethyl 4-hydroxy-2-trifluoromethylpyrimidine-5-carboxylate (51.8 g) was dissolved in dichloromethane (600 mL) under ice bath conditions. 2. Oxalyl chloride (57.4 mL) was slowly added to the above solution, followed by dimethylformamide (0.2 mL) as a catalyst. 3. The reaction mixture was stirred at room temperature for 16 hours. 4. Upon completion of the reaction, the solvent was removed by rotary evaporator. 5. Toluene was added and evaporated again to completely remove residual oxalyl chloride and by-products. 6. The residue is redissolved in methylene chloride and the organic layer is washed with water to remove water-soluble impurities. 7. The organic layer was dried using anhydrous magnesium sulfate, filtered and concentrated by rotary evaporator to afford the title compound ethyl 2-trifluoromethyl-4-chloropyrimidine-5-carboxylate as an orange oil (55.7 g, 100% yield). Product characterization data: 1H-NMR (CDCl3) δ 9.25 (1H, s), 4.51 (2H, q), 1.46 (3H, t); 13C-NMR (CDCl3) δ 126.0 (2C), 161.1, 158.1 (q, J = 39 Hz), 127.0, 118.9 (q, J = 276 Hz), 63.5, 14.4.

References

[1] Patent: US2004/167142, 2004, A1. Location in patent: Page/Page column 23
[2] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 15, p. 1645 - 1648

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