ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyrimidines Methylpyrimidine 4,6-Dichloro-2-methylpyrimidine

4,6-Dichloro-2-methylpyrimidine

Product Name4,6-Dichloro-2-methylpyrimidine
CAS1780-26-3
MFC5H4Cl2N2
MW163
EINECS605-815-0
MOL File1780-26-3.mol

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

Provider	Language
SigmaAldrich	English
ALFA	English

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

1194-22-5

1780-26-3

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

4,6-Dichloro-2-methylpyrimidine

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

4,6-Dichloro-2-methylpyrimidine Supplier

4,6-Dichloro-2-methylpyrimidine manufacturers

Related Product Information