| Identification | More | [Name]
4,6-Dichloro-2-methylpyrimidine | [CAS]
1780-26-3 | [Synonyms]
2-MDCP
2-METHYL-4,6-DICHLOROPYRIMIDINE
4,6-DICHLORO-2-METHYLPYRIMIDINE
BUTTPARK 52\14-70
4,6-Dichloro-2-methylpyrimidiine
Pyrimidine, 4,6-dichloro-2-methyl-
4,6-Dichloro-2-methylpyrimidine ,99%
4,6-Dichloro-2-Methylpyrimidine/2,4-dichloro-6-methylpyrimidine | [EINECS(EC#)]
605-815-0 | [Molecular Formula]
C5H4Cl2N2 | [MDL Number]
MFCD00090472 | [Molecular Weight]
163 | [MOL File]
1780-26-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
41.5-45.5 °C (lit.) | [Boiling point ]
210.8±20.0 °C(Predicted) | [density ]
1.404±0.06 g/cm3(Predicted) | [Fp ]
208 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
Crystalline Powder or Crystals | [pka]
-3.84±0.30(Predicted) | [color ]
White to off-white | [Detection Methods]
HPLC,NMR | [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 Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29335900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Aquatic Chronic 2
Skin Sens. 1 |
| Hazard Information | Back Directory | [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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