4,6-Dichloro-2-methylpyrimidine Chemical Properties

Melting point:

41.5-45.5 °C (lit.)

Boiling point:

210.8±20.0 °C(Predicted)

Density 

1.404±0.06 g/cm3(Predicted)

Flash point:

208 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

-3.84±0.30(Predicted)

form 

Crystalline Powder or Crystals

color 

White to off-white

InChI

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

InChIKey

FIMUTBLUWQGTIJ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

1780-26-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,N,Xn

Risk Statements 

34-51/53-43-22

Safety Statements 

26-36/37/39-45-61-36/37

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

HazardClass 

8

PackingGroup 

III

HS Code 

29335990

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Aquatic Chronic 2
Skin Sens. 1

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4,6-Dichloro-2-methylpyrimidine Usage And Synthesis

Chemical Properties

White to off-white solid

Uses

4,6-Dichloro-2-methylpyrimidine, is a versatile building block used for the synthesis of more complex pharmaceutical and biologically active compounds, such as Dasatinib (D290002), and its derivatives.

Application

The primary application of 4,6-dichloro-2-methylpyrimidine is as a key intermediate in the synthesis of the antihypertensive drug Moxonidine. Moxonidine is a centrally acting antihypertensive drug that exerts its antihypertensive effect by activating central α₂ receptors and imidazoline receptors. In its synthetic route, 4,6-dichloro-2-methylpyrimidine is used to construct the pyrimidine ring core structure, and key groups are introduced through substitution and other reactions to ultimately synthesize the target drug.

Synthesis

General procedure for the synthesis of 4,6-dichloro-2-methylpyrimidine from 6-hydroxy-2-methylpyrimidin-4-one: 4,6-dihydroxy-2-methylpyrimidine (5.0 g, 0.04 mol) was added to a mixed solution of thionyl chloride (18.9 g, 0.16 mol) with acetonitrile. The reaction mixture was stirred at 80 °C for 3 h and the completion of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, excess thionyl chloride was removed by distillation under reduced pressure and the residue was slowly poured into 50 g of ice water. The precipitated solid was filtered and purified by column chromatography to give 6.1 g (yield: 94%) of 4,6-dichloro-2-methylpyrimidine as a white solid.

References

[1] Tetrahedron Letters, 2009, vol. 50, # 41, p. 5729 - 5732
[2] Patent: CN106478519, 2017, A. Location in patent: Paragraph 0020-0023; 0030-0032; 0038-0040; 0049-0052
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 11, p. 2969 - 2973
[4] Tetrahedron, 2006, vol. 62, # 10, p. 2304 - 2312
[5] Patent: WO2004/46133, 2004, A1. Location in patent: Page 40-41

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