ethyl 2,4-dichloropyrimidine-5-carboxylate Chemical Properties

Melting point:

36-37℃

Boiling point:

145°C/11mmHg(lit.)

Density 

1.433

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

-4.47±0.29(Predicted)

form 

Powder

color 

White

Water Solubility 

Slightly soluble in water.

Stability:

Hygroscopic

InChI

InChI=1S/C7H6Cl2N2O2/c1-2-13-6(12)4-3-10-7(9)11-5(4)8/h3H,2H2,1H3

InChIKey

SRJBDGLSCPDXBL-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C(C(OCC)=O)C(Cl)=N1

Safety Information

HS Code 

2933599590

ethyl 2,4-dichloropyrimidine-5-carboxylate Usage And Synthesis

Uses

It's employed as an important intermediate for raw material for organic synthesis, agrochemical, pharmaceutical and dyestuff field

Synthesis Reference(s)

Journal of the American Chemical Society, 64, p. 794, 1942 DOI: 10.1021/ja01256a016

Synthesis

General procedure for the synthesis of ethyl 2,4-dichloro-5-pyrimidinecarboxylate from ethyl 4-hydroxy-2-oxopyrimidine-5-carboxylate: a mixture of 5-carboxyuracil (3.01 g, 16.34 mmol), POCl3 (27 mL), and N,N-diethylaniline (4.5 mL) was stirred and refluxed for 2 hr until 5-carboxyuracil was completely consumed. The reaction mixture was cooled to room temperature and then slowly poured into ice water (50 mL) and extracted with ether (2 x 100 mL). The combined ether layers were washed sequentially with saturated sodium bicarbonate solution and brine. After drying with anhydrous sodium sulfate, it was concentrated under reduced pressure to give the target product ethyl 2,4-dichloro-5-pyrimidinecarboxylate as a brown liquid in quantitative yield (3.6 g).LRMS (M+H+) m/z 221.0.

References

[1] Patent: US2009/198057, 2009, A1. Location in patent: Page/Page column 18
[2] Patent: US2006/160817, 2006, A1. Location in patent: Page/Page column 83-84
[3] Patent: US2009/264401, 2009, A1. Location in patent: Page/Page column 47
[4] Patent: CN104650045, 2017, B. Location in patent: Paragraph 0058-0060
[5] Patent: WO2011/19405, 2011, A1. Location in patent: Page/Page column 119

ethyl 2,4-dichloropyrimidine-5-carboxylate(51940-64-8)Related Product Information

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• ethyl 2,4-dichloropyrimidine-5-carboxylate