2,4-Dichloro-6-methoxypyrimidine Chemical Properties

Boiling point:

263.2±20.0 °C(Predicted)

Density 

1.446±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-4.54±0.30(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C5H4Cl2N2O/c1-10-4-2-3(6)8-5(7)9-4/h2H,1H3

InChIKey

ZSNZDRHTTWBNGI-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(OC)=CC(Cl)=N1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36

Safety Statements 

26

HS Code 

2933599590

2,4-Dichloro-6-methoxypyrimidine Usage And Synthesis

Uses

2,4-Dichloro-6-methoxypyrimidine is an intermediate used to prepare piperazinyl pyrimidine derivatives as γ-secretase modulators. It is also used in the synthesis of α-azinylalkylamino-substituted (thiazolylamino)pyrimidines and -pyrazines as selective JAK2 inhibitors.

Synthesis

General procedure for the synthesis of 2,4-dichloro-6-methoxypyrimidine from 6-methoxypyrimidine-2,4(1H,3H)-dione: 6-methoxypyrimidine-2,4(1H,3H)-dione (15 g, 0.106 mol) was mixed with phosphorus triclosan (400 ml) and heated and refluxed for 4 h. After completion of the reaction the excess of phosphorus triclosan was removed by distillation under reduced pressure. The residue was quenched with an ice-water mixture and extracted with ethyl acetate (EtOAc). The organic phases were combined, washed with water, dried over anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure to remove the solvent to afford 2,4-dichloro-6-methoxypyrimidine as an oil (5.5 g, 30% yield). Nuclear Magnetic Resonance Hydrogen Spectroscopy (NMR) data: δ 3.96 (3H, single peak), 6.63 (1H, single peak); Mass Spectrum (m/z): 179 [MH]+.

References

[1] Patent: WO2007/31745, 2007, A1. Location in patent: Page/Page column 96
[2] Organic Process Research and Development, 2012, vol. 16, # 8, p. 1416 - 1421
[3] Patent: WO2006/109026, 2006, A1. Location in patent: Page/Page column 97
[4] Patent: WO2008/117051, 2008, A1. Location in patent: Page/Page column 29
[5] Patent: WO2016/168619, 2016, A1. Location in patent: Paragraph 00162

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