Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate Chemical Properties

Melting point:

60-63 °C (lit.)

Boiling point:

132°C/0.4mmHg(lit.)

Density 

1.37±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform, Ethyl Acetate

pka

-2.19±0.29(Predicted)

form 

Crystalline Powder

color 

White to light yellow to beige

InChI

InChI=1S/C8H9ClN2O2S/c1-3-13-7(12)5-4-10-8(14-2)11-6(5)9/h4H,3H2,1-2H3

InChIKey

SNNHLSHDDGJVDM-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

5909-24-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, KEEP COLD

HS Code 

29339900

MSDS

• Language:English Provider:Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate Usage And Synthesis

Chemical Properties

off white to light yellow solid

Uses

A pyrimidine derivative as inhibitor of Streptococcus faecium, Lactobacillus casei, and Pediococcus cerevisiae

Uses

Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate was used in the synthesis of pyrimidinopyridones, potential inhibitors of the FMS tyrosine kinase.

Synthesis

General procedure for the synthesis of ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate from ethyl 4-hydroxy-2-methylthiopyrimidine-5-carboxylate: ethyl 4-hydroxy-2-methylthiopyrimidine-5-carboxylate (30 g, 140 mmol) was placed in a three-necked flask. Thionyl chloride (20 g, 168 mmol) was added slowly. The reaction system was heated to 60 °C and maintained at this temperature for 3 hours. After completion of the reaction, the reaction solution was cooled to 0-5 °C. 100 ml of ice water was slowly added and crystallization was stirred at 0-5°C for 1-2 hours. The solid product was collected by filtration and dried under vacuum at 50 °C to give 30.1 g of white solid product. The yield was 92% and the purity was 99.8% by HPLC.

References

[1] Patent: CN108101853, 2018, A. Location in patent: Paragraph 0015-0018
[2] Patent: WO2006/71940, 2006, A2. Location in patent: Page/Page column 354
[3] Patent: CN108707141, 2018, A. Location in patent: Paragraph 0027; 0030; 0039; 0048
[4] Patent: US2009/54395, 2009, A1. Location in patent: Page/Page column 45-46
[5] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 15, p. 1645 - 1648

Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate(5909-24-0)Related Product Information

• Ethyl 2-chloroacetoacetate
• ISOMETHIOZIN
• ISOXADIFEN-ETHYL
• Ethylparaben
• Ethyl acetate
• Ethanol
• Ethyl chloroacetate
• Ethyl cyanoacetate
• Ethyl acrylate
• ethyl 4-chloro-8-nitroquinoline-3-carboxylate
• 5-Pyrimidinemethanol
• ETHYL 5-PYRIMIDINECARBOXYLATE 98
• 4-Chloro-5-methylpyrimidine
• Ethyl chloroformate
• 2-Mercaptopyrimidine
• 5-Pyrimidinecarboxylic acid
• Pyrimidine-5-carboxaldehyde
• 2-(Methylthio)-5-pyrimidinecarboxylic acid ethyl ester