2-Amino-4-chloro-6-methoxypyrimidine Chemical Properties

Melting point:

168-171 °C (lit.)

Boiling point:

349.4±45.0 °C(Predicted)

Density 

1.6625 (rough estimate)

refractive index 

1.4510 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

1.96±0.10(Predicted)

form 

Crystalline Powder

color 

Light yellow

CAS DataBase Reference

5734-64-5(CAS DataBase Reference)

EPA Substance Registry System

2-Pyrimidinamine, 4-chloro-6-methoxy- (5734-64-5)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

22-2

WGK Germany 

1

RTECS 

UV6260335

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29335990

MSDS

• Language:English Provider:2-Amino-4-chloro-6-methoxypyrimidine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

2-Amino-4-chloro-6-methoxypyrimidine Usage And Synthesis

Chemical Properties

light yellow crystalline powder

Uses

2-Amino-4-chloro-6-methoxy-pyrimidine is one of the two major metabolites formed in the degradation of chlorimuron-ethyl; a pre- and post-emergence herbicide for the control of important broad-leaved weeds in soybean and maize.

Synthesis

GENERAL PROCEDURE: Intermediate Id-f was prepared similarly to Intermediate Ia-c. Anhydrous tetrahydrofuran (12 mL) solution of sodium hydride (5.8 mmol) was cooled to 0 °C under nitrogen protection, followed by slow dropwise addition of substitutional alcohol (6.1 mmol). The reaction mixture was kept stirred at 0 °C for 15 min. Then, 2-amino-4,6-dichloropyrimidine (5.8 mmol) was added to the reaction system. The reaction temperature was raised to 62°C and the reaction was continued for 15 hours. After completion of the reaction, the mixture was cooled to room temperature and the reaction was quenched with 1 M hydrochloric acid solution (1 mL). The reaction mixture was diluted with ethyl acetate (20 mL), washed twice sequentially with saturated sodium bicarbonate solution (20 mL) and brine (20 mL), and the organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure. Finally, the residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether as eluent) to afford the target compound Id-f. 4-Chloro-6-methoxypyrimidin-2-amine (Id) was a white solid with a melting point of 165-167 °C in 84% yield.1H-NMR (CDCl3) δ 6.04 (s, 1H, ArH), 5.35-5.14 (m, 2H , NH2), 3.81 (s, 3H, OCH3).

References

[1] Patent: WO2004/37795, 2004, A1. Location in patent: Page/Page column 8
[2] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 10, p. 774 - 779
[3] Molecules, 2018, vol. 23, # 9,
[4] Nippon Kagaku Zasshi, 1953, vol. 74, p. 624
[5] Chem.Abstr., 1954, p. 13693

2-Amino-4-chloro-6-methoxypyrimidine(5734-64-5)Related Product Information

• ALTRENOGEST
• p-Anisaldehyde
• 4-Methoxybenzylchloride
• 2-Amino-4-chloropyrimidine
• (Trifluoromethoxy)benzene
• 2-Amino-4,6-dimethoxypyrimidine
• 3-Aminophenol
• 6-Aminocaproic acid
• 2-Aminopyrimidine
• Glycine
• Anisole
• 4-Amino-6-methoxypyrimidine
• 2-Methylsulfonyl-4,6-dimethoxypyrimidine
• 2-Amino-4-methoxy-6-methyl-1,3,5-triazine
• 2-Amino-4,6-dimethylpyrimidine
• Tris(hydroxymethyl)aminomethane
• 2-Aminobenzylchloride
• Difluorochloromethane