| Identification | More | [Name]
4,6-Dichloro-2-(methylsulfonyl)pyrimidine | [CAS]
4489-34-3 | [Synonyms]
2-METHANESULFONYL-4,6-DIMETHYL-PYRIMIDINE
2-(methylsulfonyl)-4,6-dichloropyrimidine
2-(methylsulfonyl)-4,6-dimethylpyrimidine
4,6-DICHLORO-2-(METHYLSULFONYL)PYRIMIDINE
4,6-DIMETHY-2-METHYLSULFONYLPYRIMIDINE
4,6-DIMETHYL-2-METHYLSULFONYLPYRIMIDINE
DLMSP
nsc 45040
PYRIMIDINE, 4,6-DICHLORO-2-(METHYLSULFONYL)-
VITAS-BB TBB000242
4,6-DICHLORO-2-METHANESULFONYLPYRIMIDINE
4,6-DIMETHYL-2-METHYLSULFONYLPYRIMIDINE, 98+%
4,6-Dichloro-2-(methylsulfonyl)pyrimidine ,98% | [Molecular Formula]
C5H4Cl2N2O2S | [MDL Number]
MFCD03788286 | [Molecular Weight]
227.07 | [MOL File]
4489-34-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
117-118°C | [Boiling point ]
402.3±48.0 °C(Predicted) | [density ]
1.604 | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
-9.08±0.30(Predicted) | [color ]
White to Yellow to Orange | [Detection Methods]
HPLC | [InChI]
InChI=1S/C5H4Cl2N2O2S/c1-12(10,11)5-8-3(6)2-4(7)9-5/h2H,1H3 | [InChIKey]
DROUVIKCNOHKBA-UHFFFAOYSA-N | [SMILES]
C1(S(C)(=O)=O)=NC(Cl)=CC(Cl)=N1 | [CAS DataBase Reference]
4489-34-3(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Synthesis]
The general procedure for the synthesis of 4,6-dichloro-2-(methylsulfonyl)pyrimidines from 4,6-dichloro-2-methylthioalkylpyrimidines is as follows:
Example 27: Synthesis of 4,6-dichloro-2-(methylsulfonyl)pyrimidine
Commercially available 4,6-dichloro-2-methylsulfanylpyrimidine (Aldrich, 21.0 g, 107.0 mmol, 1 eq.) was dissolved in dichloromethane and cooled in an ice bath. Subsequently, 3-chloroperoxybenzoic acid (60.0 g, 77% wt, 268.0 mmol, 2.5 eq.) was added in batches. The resulting white suspension was stirred at room temperature for 4 hours. Upon completion of the reaction, it was washed sequentially with a mixture of 1 M sodium thiosulfate solution and saturated sodium bicarbonate solution (1:1, v/v, 200 mL x 3), saturated sodium bicarbonate solution (100 mL x 3) and brine (100 mL x 1). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The product was dried under high vacuum overnight to give the title compound EPO27 as a white solid (22.0 g, 91% yield). Thin layer chromatography Rf value was 0.20 (unfolding agent: 20% ethyl acetate/hexane); mass spectrum m/z 227 (calculated value 227, corresponding to molecular formula C5H4Cl2N2O2S+). | [References]
[1] Patent: WO2007/14250, 2007, A2. Location in patent: Page/Page column 17-18
[2] Patent: WO2007/87245, 2007, A2. Location in patent: Page/Page column 27
[3] Patent: WO2007/87246, 2007, A2. Location in patent: Page/Page column 27
[4] Patent: WO2008/13807, 2008, A2. Location in patent: Page/Page column 6
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 28, p. 8153 - 8157 |
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