2-Methanesulfonyl-4,6-dimethoxypyrimidine Chemical Properties

Melting point:

129-133 °C(lit.)

Boiling point:

412.6±48.0 °C(Predicted)

Density 

1.317±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

-3.39±0.30(Predicted)

color 

Whtie

InChI

InChI=1S/C7H10N2O4S/c1-12-5-4-6(13-2)9-7(8-5)14(3,10)11/h4H,1-3H3

InChIKey

ITDVJJVNAASTRS-UHFFFAOYSA-N

SMILES

C1(S(C)(=O)=O)=NC(OC)=CC(OC)=N1

CAS DataBase Reference

113583-35-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29335990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

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

Chemical Properties

White to off-white powder

Uses

4,6-Dimethoxy-2-(methylsulfonyl)pyrimidine may be used in the microwave assisted preparation of 4,6-dimethoxy-N-methylpyrimidin-2-amine by reacting with methylamine. It may also be used to prepare 2′-pyrimidinecarbonylsulfonanilide derivatives with potent herbicidal activity.

Uses

2-Methanesulfonyl-4,6-dimethoxypyrimidine was used to prepare nonpeptidic endothelin-A receptor antagonists.

Preparation

One method for preparing 2-Methanesulfonyl-4,6-dimethoxypyrimidine comprises with 4, 6-dihydroxyl-2-methylthiopyrimidine is a main raw material, and through superchlorination, methoxylation and oxidizing reaction, reaction formula is as follows:

General Description

4,6-Dimethoxy-2-(methylsulfonyl)pyrimidine can be prepared by the oxidation of 2-methylthio-4,6-dimethoxypyrimidine.

Synthesis

Example 10: Synthesis of 4,6-dimethoxy-2-(methylsulfonyl)pyrimidine To 200 mL of acetic acid was added 3% sodium tungstate as a catalyst. Subsequently, 1.0 mol of 2-methylsulfanyl-4,6-dimethoxypyrimidine was added to the solution and stirred until completely dissolved to form a clarified solution. The reaction mixture was heated to 40°C. Over a period of 4-8 hours, 2.1 mol of 30% H2O2 solution was slowly added to the heated reaction mixture and stirring was continued at 40 °C for 3-5 hours. After that, 0.05 mol of 30% H2O2 solution was added supplementally and stirring was continued at the same temperature until the reaction was complete (the progress of the reaction was monitored by TLC or HPLC). After completion of the reaction, the reaction mixture was cooled to room temperature and the precipitated solid was collected by filtration. The resulting solid was washed sequentially with aqueous acetic acid and deionized water to remove impurities. Finally, the washed solid was dried under appropriate conditions to obtain the target product in 83% yield. The filtrate portion was extracted with dichloroethane, and after separating the organic layer, the dichloroethane layer was concentrated to give a residue of about 42 g containing a small amount of product in about 1-1.5% yield.

References

[1] Asian Journal of Chemistry, 2014, vol. 26, # 1, p. 313 - 314
[2] Journal of Agricultural and Food Chemistry, 2018, vol. 66, # 15, p. 3773 - 3782
[3] Pesticide Science, 1996, vol. 47, # 2, p. 115 - 124
[4] Patent: WO2014/128719, 2014, A2. Location in patent: Page/Page column 17
[5] Journal of Labelled Compounds and Radiopharmaceuticals, 2006, vol. 49, # 4, p. 339 - 343

2-Methanesulfonyl-4,6-dimethoxypyrimidine(113583-35-0)Related Product Information

• 2-Amino-4,6-dimethylpyrimidine
• 4,6-Dimethoxy-2-(phenoxycarbonyl)aminopyrimidine
• (Trifluoromethoxy)benzene
• m-Anisyl alcohol
• Methoxyacetic acid
• Anisole
• Dimethyldimethoxysilane
• p-Anisidine
• 2,6-Dihydroxybenzoic acid
• 2-Mercapto-4,6-dimethoxypyrimidine
• 4,6-Dimethoxypyrimidine
• SULFACHLOROPYRIDAZINE
• Methanesulfonic acid
• 4,6-DIMETHOXY-2-(METHYLSULFONYL)PYRIMIDINE
• 2-METHANESULFONYL-PYRIMIDINE
• 4,6-Dimethoxy-2-methylthiopyrimidine
• 4,6-Dimethylpyrimidine-2-sulfonamide
• 2-Methylthio-4,6-pyrimidinedione