2,4-Dichloro-5-methylpyrimidine Chemical Properties

Melting point:

26-28 °C (lit.)

Boiling point:

108-109 °C/11 mmHg (lit.)

Density 

1.39 g/mL at 25 °C (lit.)

refractive index 

1.6300 (estimate)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Soluble in chloroform, ether, ethyl acetate and toluene

form 

powder to lump to clear liquid

pka

-2.44±0.29(Predicted)

color 

White or Colorless to Almost white or Almost colorless

Sensitive 

Lachrymatory

InChI

InChI=1S/C5H4Cl2N2/c1-3-2-8-5(7)9-4(3)6/h2H,1H3

InChIKey

DQXNTSXKIUZJJS-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

1780-31-0(CAS DataBase Reference)

EPA Substance Registry System

Pyrimidine, 2,4-dichloro-5-methyl- (1780-31-0)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45-27

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29335990

MSDS

• Language:English Provider:2,4-Dichloro-5-methylpyrimidine
• Language:English Provider:SigmaAldrich

2,4-Dichloro-5-methylpyrimidine Usage And Synthesis

Chemical Properties

White to Off White Low Melting Solid

Uses

2,4-Dichloro-5-methylpyrimidine, is used in the synthesis of (2-chloro-6-methyl-pyrimidin-4-yl)-(2,3-dihydro-benzothiazol-6-yl)-amine. It can react with piperidineto produce 2-chloro-5-methyl-4-piperidin-1-yl-pyrimidine. This reaction will need solvent dioxane.

Synthesis

General procedure for the synthesis of 2,4-dichloro-5-methylpyrimidine from 5-methyluracil: 5-methyluracil (1 g, 7.93 mmol) was added to phosphorochloridic acid (7 eq., 5 ml), and the mixture was heated and refluxed for 3 hours. After completion of the reaction, the mixture was slowly poured into ice water to quench the reaction. The organic layer was extracted with chloroform (3 x 20 ml), the organic phases were combined and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 2,4-dichloro-5-methylpyrimidine as yellow crystals (0.62 g, 48% yield). The structure of the product was confirmed by nuclear magnetic resonance hydrogen (1H NMR, 400 MHz, CDCl3) and carbon (13C NMR, 100 MHz, CDCl3) spectra: 1H NMR δ 8.35 (s, 1H), 2.39 (s, 3H); 13C NMR δ 162.5, 160.0, 158.2, 129.1, 15.8. The data obtained were in agreement with those of literature reports (Wang et al., Molecules, 2012, 17(4), 4533-4544).

References

[1] Journal of Fluorine Chemistry, 1996, vol. 77, # 1, p. 93 - 95
[2] Patent: WO2018/151681, 2018, A1. Location in patent: Paragraph 0099
[3] Synthetic Communications, 1992, vol. 22, # 20, p. 2927 - 2934
[4] Tetrahedron Letters, 1997, vol. 38, # 7, p. 1111 - 1114
[5] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 18, p. 2961 - 2966

2,4-Dichloro-5-methylpyrimidine(1780-31-0)Related Product Information

• Pirimiphos-methyl
• 4,6-Dichloropyrimidine
• Fluorocytosine
• 2,4-Dichloropyrimidine
• 4-Ethyl-5-fluoro-6-hydroxypyrimidine
• Dichloromethylphenylsilane
• Dichloromethylsilane
• 2,4-Dichloro-5-nitropyrimidine
• 2-Chloro-5-chloromethylpyridine
• 2,4-Dichloro-5-fluoropyrimidine
• Dichlorodimethylsilane
• Dichloroacetic acid
• (9H-FLUOREN-9-YL)METHYL 2,4-DICHLORO-5H-PYRROLO[3,4-D]PYRIMIDINE-6(7H)-CARBOXYLATE
• 2,4-Dichloro-5-cyanopyrimidine
• 2,4,6-TRICHLORO-PYRIMIDINE-5-CARBALDEHYDE
• 2,4-Dichloro-5-pyrimidinecarbonyl chloride
• (9H-FLUOREN-9-YL)METHYL 2,4-DICHLORO-7,8-DIHYDROPYRIDO[4,3-D]PYRIMIDINE-6(5H)-CARBOXYLATE
• tert-Butyl 2,4-dichloro-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate