Ethyl 2-chloropyrimidine-5-carboxylate Chemical Properties

Melting point:

52-60℃

Boiling point:

80℃/760mm

Density 

1.311±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

soluble in Methanol

pka

-3.05±0.22(Predicted)

form 

Solid

color 

White to Light yellow

InChI

InChI=1S/C7H7ClN2O2/c1-2-12-6(11)5-3-9-7(8)10-4-5/h3-4H,2H2,1H3

InChIKey

IEMKQRSOAOPKRJ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

89793-12-4

Safety Information

Risk Statements 

20/21/22

Safety Statements 

36/37

HazardClass 

IRRITANT

HS Code 

29339900

Ethyl 2-chloropyrimidine-5-carboxylate Usage And Synthesis

Chemical Properties

White to light yellow liquid

Uses

Ethyl 2-chloropyrimidine-5-carboxylate is used in the synthesis of Retinoid x receptor agonists (RXR) that are used in the treatment of cancers.

Synthesis

A mixture of 1,2-Dihydro-2-oxo-5-pyrimidinecarboxylic acid ethyl ester (3.60 g, 21 mmol), phosphorus oxychloride (25 mL), and N, N-dimethylaniline (2.5 mL) was heated to reflux for 1.5 h. After removal of the solvent, ice water (10 mL) was added to the residue. The mixture was added to 2 N NaOH (90 ml) and extracted with EtOAc. After work, the residue was purified by column chromatography on silica gel (ethyl acetate in petroleum ether, 5 per cent v/v) to give the product Ethyl 2-chloropyrimidine-5-carboxylate (1.20 g, 30 per cent).

References

[1] Patent: US9249156, 2016, B2. Location in patent: Page/Page column 34
[2] Patent: WO2018/85342, 2018, A1. Location in patent: Page/Page column 26; 27; 28
[3] Patent: US2009/76006, 2009, A1. Location in patent: Page/Page column 31; 40
[4] Patent: WO2011/130628, 2011, A1. Location in patent: Page/Page column 138-139
[5] Patent: WO2009/36016, 2009, A1. Location in patent: Page/Page column 69

Ethyl 2-chloropyrimidine-5-carboxylate(89793-12-4)Related Product Information

• 4,6-Dihydroxypyrimidine
• 2,5-PYRIDINEDICARBOXYLIC ACID
• 2-Chloropyrimidine
• 2-Chloropyrimidine-5-carboxylic acid
• ethyl 2-chloro-4-(1-methylethyl)pyrimidine-5-carboxylate
• BENZYL 2-CHLORO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
• ethyl 2-chloro-4-ethylpyrimidine-5-carboxylate
• Ethyl 2-chloropyrimidine-5-carboxylate
• ETHYL 2-CHLORO-4-PHENYLPYRIMIDINE-5-CARBOXYLATE
• ETHYL-2-CHLORO-4-METHYL-5-PYRIMIDINECARBOXYLATE
• CYCLOPROPYLMETHYL 2-CHLORO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
• 4-CHLOROBENZYL 2-CHLORO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
• ETHYL 2-CHLORO-4-(N-ETHOXYCABONYLETHYL-N-ETHYLAMINO) PYRIMIDINE-5-CARBOXYLATE
• ETHYL 2-CHLORO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
• ethyl 4-tert-butyl-2-chloropyrimidine-5-carboxylate
• ethyl 2,4-dichloropyrimidine-5-carboxylate