4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXYLIC ACID Chemical Properties

Melting point:

159-163 °C (D)

Boiling point:

384.5±37.0 °C(Predicted)

Density 

1.71±0.1 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

0.08±0.32(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C6H4Cl2N2O2S/c1-13-6-9-3(7)2(5(11)12)4(8)10-6/h1H3,(H,11,12)

InChIKey

LUCAXEBLTQAMHS-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXYLIC ACID Usage And Synthesis

Synthesis

1. 4,6-dichloro-2-methylthioalkylpyrimidine (1.00 g, 5.13 mmol) was dissolved in tetrahydrofuran (THF, 10 mL). 2. 2.0 M lithium diisopropylammonium (LDA) solution in THF (5.9 mL, 11.8 mmol) was added to the solution at -78 °C and stirred for 1 hour. 3. carbon dioxide gas (dry ice) was passed into the reaction mixture at -78 °C. 4. the reaction mixture was warmed to room temperature and stirring was continued for 1.5 hours. 5. Upon completion of the reaction, the organic layer was separated by adding 10% aqueous hydrochloric acid and ethyl acetate for extraction. 6. The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. 7. The residue was re-slurried with hexane and the solid was collected by filtration to afford 2-(methylthio)-4,6-dichloropyrimidine-5-carboxylic acid (964 mg, 79% yield). 8. The product was passed through ESI-MSR. 8. The product was characterized by ESI-MS and 1H-NMR: ESI-MS m/z 237 [M-H]-; 1H-NMR (CDCl3) δ 2.60 (s, 3H), 9.68 (brs, 1H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 16, p. 4642 - 4646
[2] Patent: EP2163554, 2010, A1. Location in patent: Page/Page column 49
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 5, p. 1485 - 1488
[4] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 20, p. 5717 - 5732
[5] Patent: EP1496059, 2005, A1. Location in patent: Page 19-20

4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXYLIC ACID(313339-35-4)Related Product Information

• 4,6-Dichloro-2-(methylthio)pyrimidine
• 4,6-DICHLORO-2-METHYLSULFANYL-PYRIMIDINE-5-CARBALDEHYDE
• 4-CHLOROPYRIMIDINE-5-CARBOXYLIC ACID
• 4,6-dichloropyrimidine-5-carboxylic acid
• 4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXYLIC ACID
• 4,6-Dichloro-5-pyrimidinecarbaldehyde
• 4-Chloro-6-methyl-2-(methylthio)pyrimidine