| Identification | Back Directory | [Name]
4,6-Dichloro-2-Methylsulfanyl-5-nitro-pyriMidine | [CAS]
1979-96-0 | [Synonyms]
2-Methylthio-4,6-dichloro-5-nitro-pyriMidine
4,6-Dichloro-2-(Methylthio)-5-nitropyriMidine
Pyrimidine, 4,6-dichloro-2-(methylthio)-5-nitro-
4,6-Dichloro-2-Methylsulfanyl-5-nitro-pyriMidine
4,6-Dichloro-2-(methylthio)-5-nitropyrimidine 98%
4,6-Dichloro-2-Methylsulfanyl-5-nitro-pyriMidine-3
4,6-Dichloro-2-Methylsulfanyl-5-nitro-pyriMidine ISO 9001：2015 REACH | [Molecular Formula]
C5H3Cl2N3O2S | [MDL Number]
MFCD02323208 | [MOL File]
1979-96-0.mol | [Molecular Weight]
240.07 |
| Chemical Properties | Back Directory | [Melting point ]
61 °C | [Boiling point ]
360.4±37.0 °C(Predicted) | [density ]
1.70±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [pka]
-8.04±0.39(Predicted) | [Appearance]
White to light yellow Solid | [InChI]
InChI=1S/C5H3Cl2N3O2S/c1-13-5-8-3(6)2(10(11)12)4(7)9-5/h1H3 | [InChIKey]
GHAWBARMICSLQS-UHFFFAOYSA-N | [SMILES]
C1(SC)=NC(Cl)=C([N+]([O-])=O)C(Cl)=N1 |
| Hazard Information | Back Directory | [Uses]
4,6-Dichloro-2-(methylthio)-5-nitro-pyrimidine is a useful synthetic intermediate. It is used to prepare Cathepsin K inhibition SAR. It is also used to synthesize GS39783 (G797150) which is an allosteric positive modulator of GABAB receptors. | [Synthesis]
Step 2: 4,6-Dihydroxy-2-methylthio-5-nitropyrimidine (9.30 g, 45.81 mmol) was mixed with phosphorus trichloride (40 mL) and diethylaniline (12 mL) and the reaction was carried out at reflux for 1 hour. Upon completion of the reaction, the reaction mixture was partially evaporated, followed by slow pouring of the remaining liquid into ice water to precipitate a brown solid. The solid product was collected by filtration and washed well with cold water. The resulting solid was dried under vacuum to afford 4,6-dichloro-2-methylthio-5-nitropyrimidine (10.5 g, 95% yield) as a brown solid. Low resolution mass spectra (LRMS) of the product showed m/z = 240 (corresponding to the [M + H]+ ion of C5H3Cl2N3O2S). Nuclear magnetic resonance (NMR) spectral analysis showed results consistent with the structure of the target compound. | [References]
[1] Patent: US2007/270433, 2007, A1. Location in patent: Page/Page column 51
[2] Patent: US2008/4253, 2008, A1. Location in patent: Page/Page column 13
[3] Patent: US2009/156599, 2009, A1. Location in patent: Page/Page column 12
[4] Patent: WO2013/68438, 2013, A1. Location in patent: Page/Page column 29-30
[5] Patent: US2010/143301, 2010, A1. Location in patent: Page/Page column 45-46 |
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