4,6-Dichloro-2-Methylsulfanyl-5-nitro-pyriMidine Chemical Properties

Melting point:

61 °C

Boiling point:

360.4±37.0 °C(Predicted)

Density 

1.70±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 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

Safety Information

HS Code 

2933599590

4,6-Dichloro-2-Methylsulfanyl-5-nitro-pyriMidine Usage And Synthesis

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