| Identification | Back Directory | [Name]
2,4-dichloro-5-MethylsulfanylpyriMidine | [CAS]
7401-98-1 | [Synonyms]
2,4-dichloro-5-mercapto-pyrimidine 1,3-dichloro-4-(methylthio)pyrimidine 2,4-Dichloro-5-(methylthio)pyrimidine 2,4-dichloro-5-MethylsulfanylpyriMidine PyriMidine, 2,4-dichloro-5-(Methylthio)- 2,4-Dichloro-5-(methylsulphanyl)pyrimidine | [Molecular Formula]
C5H4Cl2N2S | [MDL Number]
MFCD22199809 | [MOL File]
7401-98-1.mol | [Molecular Weight]
195.07 |
| Chemical Properties | Back Directory | [Boiling point ]
282.7±25.0 °C(Predicted) | [density ]
1.51±0.1 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
solid | [pka]
-3.19±0.29(Predicted) | [color ]
Off-white to light yellow | [InChI]
InChI=1S/C5H4Cl2N2S/c1-10-3-2-8-5(7)9-4(3)6/h2H,1H3 | [InChIKey]
PQLHCTKAQZYUMI-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC=C(SC)C(Cl)=N1 |
| Hazard Information | Back Directory | [Uses]
2,4-Dichloro-5-(methylsulfanyl)pyrimidine is used in preparation of the bridged heterocyclyl-substituted pyrimidine compounds and their pharmaceutical applications. | [Synthesis]
5-(Methylthio)pyrimidine-2,4(1H,3H)-dione (600 mg, 3.8 mmol) was used as a raw material and prepared according to the method described by Kopp F et al. in Organic Letters, 2007, 9, 1639-41. The raw material was dissolved in phosphoryl chloride (15 mL) and the reaction was stirred at 100 °C for 16 hours. Upon completion of the reaction, the reaction mixture was quenched by slowly pouring it into ice water. The mixture was subsequently extracted with dichloromethane (20 mL × 2), and the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (eluent: dichloromethane/tetrahydrofuran = 100:100) to afford 2,4-dichloro-5-(methylthio)pyrimidine (520 mg, 70% yield) as a yellow oil. | [References]
[1] Patent: WO2015/89218, 2015, A1. Location in patent: Page/Page column 127; 128 [2] Patent: CN104583195, 2018, B. Location in patent: Paragraph 0369; 0370; 0374; 0375; 0376 [3] Patent: US2003/171359, 2003, A1. Location in patent: Page 29 [4] Journal of Medicinal Chemistry, 2014, vol. 57, # 19, p. 8099 - 8110 |
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