2-Chloro-4,6-dimethoxypyrimidine Chemical Properties

Melting point:

100-105 °C

Boiling point:

317.1±22.0 °C(Predicted)

Density 

1.285±0.06 g/cm3(Predicted)

storage temp. 

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

form 

powder to crystal

pka

-1.46±0.30(Predicted)

color 

White to Light yellow

BRN 

880035

InChIKey

PBEKEFWBLFBSGQ-UHFFFAOYSA-N

CAS DataBase Reference

13223-25-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36-36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

29335990

MSDS

• Language:English Provider:SigmaAldrich

2-Chloro-4,6-dimethoxypyrimidine Usage And Synthesis

Chemical Properties

White Powder

Uses

2-Chloro-4,6-dimethoxypyrimidine is used as building block in chemical synthesis. Product Data Sheet

Uses

2-Chloro-4,6-dimethoxypyrimidine is a useful reactant for the synthesis of polycyclic fused and spiro-?4-?aminopyridines

Synthesis

General procedure for the synthesis of 2-chloro-4,6-dimethoxypyrimidine from 2-amino-4,6-dimethoxypyrimidine: 1. 1,260 ml of 36% hydrochloric acid was added to a 5-liter four-necked flask and subsequently cooled to 0°C. 2. 180 g (1.16 moles) of 2-amino-4,6-dimethoxypyrimidine was added to the flask in batches and stirred continuously for about 1 hour until the reaction mixture took on a syrupy consistency. 3. After the reaction mixture was further cooled to -15°C, 260 ml of an aqueous solution containing 159 g (2.3 moles) of NaNO2 was slowly added dropwise over a period of about 1 hour under vigorous stirring. 4. after completion of the dropwise addition, the mixture was continued to be stirred at -15°C to -10°C for 1 hour to ensure complete reaction. 5. While keeping the reaction mixture at -5°C, 1.5 liters of 30% aqueous NaOH was slowly added dropwise to adjust the pH to 7 for neutralization. 6. The resulting purple clay-like substance was collected by filtration under reduced pressure. 7. the target compound 2-chloro-4,6-dimethoxypyrimidine was extracted from the clay-like material using 3 liters of ethyl acetate. 8. The organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was removed to yield 63 g of light blue crude crystals. 9. Purification and crystallization by silica gel chromatography resulted in 60.8 g of white crystals (yield: 29.9%) with a melting point of 101.5°-102.5°C. The final product was purified by silica gel chromatography.

References

[1] Patent: US4986846, 1991, A
[2] Pesticide Science, 1996, vol. 47, # 2, p. 103 - 114

2-Chloro-4,6-dimethoxypyrimidine(13223-25-1)Related Product Information

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• 2,6-Dimethoxybenzaldehyde
• Diphenyldimethoxysilane
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• Difluorochloromethane
• 2-CHLORO-4-METHOXYPYRIMIDINE
• 4-CHLORO-2,6-DIMETHOXYPYRIMIDINE,6-CHLORO-2,4-DIMETHOXYPYRIMIDINE,6-CHLORO-2,4-DIMETHOXYPYRIMIDINE, 98+%
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• 2-CHLORO-4,6-DIMETHOXY-5-NITRO-PYRIMIDINE
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• 5-CHLORO-4,6-DIMETHOXYPYRIMIDINE