2-Chloro-4,5-diMethoxy-pyriMidine

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2-Chloro-4,5-diMethoxy-pyriMidine Basic information
Product Name:2-Chloro-4,5-diMethoxy-pyriMidine
Synonyms:2-Chloro-4,5-diMethoxy-pyriMidine;Pyrimidine, 2-chloro-4,5-dimethoxy-
CAS:1333240-17-7
MF:C6H7ClN2O2
MW:174.59
EINECS:
Product Categories:
Mol File:1333240-17-7.mol
2-Chloro-4,5-diMethoxy-pyriMidine Structure
2-Chloro-4,5-diMethoxy-pyriMidine Chemical Properties
Boiling point 290.9±20.0 °C(Predicted)
density 1.285±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
pka0.23±0.29(Predicted)
AppearanceWhite to light yellow Solid
Safety Information
MSDS Information
2-Chloro-4,5-diMethoxy-pyriMidine Usage And Synthesis
Uses2-Chloro-4,5-dimethoxypyrimidine is used as a reactant in the preparation of aryl-substituted 4-hydroxypyridazin-3(2H)-ones and 5-hydroxypyrimidin-4(3H)-ones as inhibitors of influenza A endonuclease.
Synthesis
Methanol

67-56-1

2,4-Dichloro-5-methoxypyrimidine

19646-07-2

2-Chloro-4,5-diMethoxy-pyriMidine

1333240-17-7

1. Preparation of the compound 2-chloro-4,5-dimethoxypyrimidine: 2,4-dichloro-5-methoxypyrimidine (2.37 g, 13.2 mmol) and potassium carbonate (K2CO3, 1.8 g, 13.2 mmol) were dissolved in methanol (MeOH, 50 mL), and the reaction was stirred for 19 hours at room temperature. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting residue was dissolved in ethyl acetate (EtOAc) and washed sequentially with distilled water and saturated saline. The organic layer was dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. Subsequently, purification was carried out by silica gel column chromatography with 0 to 20% ethyl acetate/hexane as eluent to afford the target product 2-chloro-4,5-dimethoxypyrimidine as a white solid (1.70 g, 73% yield). The product was characterized by the following data: melting point 65-67 °C; 1H NMR (400 MHz, CDCl3) δ 7.84 (s, 1H), 4.03 (s, 3H), 3.88 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 161.2, 150.0, 141.7, 138.2, 56.6, 55.0.

References[1] Patent: WO2014/43252, 2014, A2. Location in patent: Page/Page column 64
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 19, p. 8086 - 8098
[3] Patent: WO2011/109267, 2011, A1. Location in patent: Page/Page column 46-47
2-Chloro-4,5-diMethoxy-pyriMidine Preparation Products And Raw materials
Raw materialsMethanol-->2,4-Dichloro-5-methoxypyrimidine
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