Ethyl 4-pyrimidinecarboxylate Chemical Properties

Melting point:

37.0 to 41.0 °C

Boiling point:

240 ºC

Density 

1.167

Flash point:

99 ºC

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to lump

pka

-0.76±0.10(Predicted)

color 

White to Orange to Green

CAS DataBase Reference

62846-82-6(CAS DataBase Reference)

Safety Information

HS Code 

2933599590

Ethyl 4-pyrimidinecarboxylate Usage And Synthesis

Synthesis

General procedure for the synthesis of ethyl 4-pyrimidinecarboxylate from pyrimidine-4-carboxylic acid and ethanol: Thionyl chloride (3.55 mL, 48.4 mmol, 3 eq.) was slowly added dropwise to a solution of pyrimidine-4-carboxylic acid (2 g, 16.1 mmol) in anhydrous ethanol (15 mL). The reaction mixture was heated to reflux for 14 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted with saturated aqueous sodium bicarbonate solution to 8. Subsequently, the reaction mixture was extracted with ethyl acetate (4 x 50 mL). The organic phases were combined, washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give Intermediate 23 (1.7 g, 77% yield). The product was confirmed by 1H NMR (DMSO-d6): δ 9.40 (d, J = 1.0 Hz, 1H), 9.10 (d, J = 5.1 Hz, 1H), 8.05 (dd, J = 5.1, 1.3 Hz, 1H), 4.39 (q, J = 7.1 Hz, 2H), 1.35 (t, J = 7.1 Hz, 3H); mass spectrum (MS): m/ z 153 [M + H]+; thin layer chromatography (TLC) conditions: 40% hexane/ethyl acetate, Rf = 0.40.

References

[1] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2676 - 2699
[2] Patent: WO2011/126903, 2011, A2. Location in patent: Page/Page column 92
[3] Patent: WO2014/145986, 2014, A1. Location in patent: Paragraph 0242; 0243
[4] Patent: US2017/326125, 2017, A1. Location in patent: Paragraph 0359-0361
[5] Bulletin des Societes Chimiques Belges, 1957, vol. 66, p. 276,289

Ethyl 4-pyrimidinecarboxylate(62846-82-6)Related Product Information

• Triethyl orthoformate
• Ethyl cyanoformate
• Ethyl cyanoacetate
• Ethylparaben
• Ethyl acrylate
• Sulfadimethoxine sodium salt
• Urethane
• Ethyl propiolate
• Ethyl acetate
• Ethanol
• Trinexapac-ethyl
• ISOXADIFEN-ETHYL
• Benzocaine
• Ethyl formate
• 4-Pyrimidinecarboxylic acid
• Ethyl chloroformate
• Ethyl 4-pyrimidinecarboxylate
• Poly-AminoEthylFormate