| Identification | Back Directory | [Name]
2-CHLORO-4-METHYLSULFANYL-PYRIMIDINE | [CAS]
49844-93-1 | [Synonyms]
2-CHLORO-4-METHYLSULFANYL-PYRIMIDINE
Pyrimidine, 2-chloro-4-(methylthio)-
2-CHLORO-4-METHYLSULFANYL-PYRIMIDINE ISO 9001：2015 REACH
2-Chloro-4-(methylsulphanyl)pyrimidine, 2-Chloro-4-(methylsulphonyl)-1,3-diazine | [Molecular Formula]
C5H5ClN2S | [MDL Number]
MFCD09265490
| [MOL File]
49844-93-1.mol | [Molecular Weight]
160.625 |
| Chemical Properties | Back Directory | [Melting point ]
67-68 °C | [Boiling point ]
125-126 °C(Press: 15 Torr) | [density ]
1.37±0.1 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
solid | [pka]
-0.45±0.20(Predicted) | [color ]
white |
| Hazard Information | Back Directory | [Synthesis]
At -10 °C, 2,4-dichloropyrimidine (20.0 g, 0.13 mol) was dissolved in 150 mL of anhydrous tetrahydrofuran, and sodium methanethiol (49.30 mL, 0.15 mol) was added slowly. The reaction mixture was gradually warmed up to room temperature with continuous stirring for 5 h, during which the reaction progress was monitored by liquid chromatography-mass spectrometry (LC-MS) or thin-layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed twice with saturated saline (x2). The organic layers were combined, dried with anhydrous sodium sulfate and subsequently concentrated under reduced pressure. The resulting solid was recrystallized with ether and collected by filtration to afford the target product 2-chloro-4-methylthiopyrimidine (Intermediate 10) as a white solid (11.2 g, 52% yield). | [References]
[1] Journal of Heterocyclic Chemistry, 2007, vol. 44, # 4, p. 967 - 971
[2] Organic Letters, 2016, vol. 18, # 9, p. 2180 - 2183
[3] Patent: WO2013/109882, 2013, A1. Location in patent: Page/Page column 63
[4] Patent: US2016/83365, 2016, A1. Location in patent: Paragraph 0841-0843
[5] Journal of Organic Chemistry, 2017, vol. 82, # 5, p. 2664 - 2671 |
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