Epirizole Chemical Properties

Melting point:

90-92°

Boiling point:

376.57°C (rough estimate)

Density 

1.1972 (rough estimate)

refractive index 

1.6000 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

0.65±0.50(Predicted)

form 

Solid

color 

White to off-white

CAS DataBase Reference

18694-40-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

UV9290000

Toxicity

LD50 orally in mice: 820 mg/kg (Ogura)

MSDS

• Language:English Provider:2-(5-Methoxy-3-methyl-1-pyrazinyl)-4-methoxy-6-methyl-pyrimidine
• Language:English Provider:SigmaAldrich

Epirizole Usage And Synthesis

Originator

Mebron,Daiichi Seiyaku,Japan,1970

Uses

Analgesic; anti-inflammatory.

Uses

Mepirizole induces precocious differentiation of insulin-producing ti-cells in larval zebrafish. Also, it increases the expression of MDR1 mRNA in Caco-2 cells; Non-acidic analgesic.

Definition

ChEBI: Epirizole is an aromatic ether.

Manufacturing Process

A mixture of 16.3 g of 4-methyl-6-methoxy-2-pyrimidinyl-hydrazine,13.7 g of ethyl acetoacetate and 16.3 ml of methanol was refluxed 2 hours on a water bath. After a mixture of 4.7 g of sodium hydroxide, 4.7 ml of water and 27 ml of methanol was added dropwise thereto at about 50°C, the reaction mixture was refluxed for 2 hours more, then methanol was distilled off and the residue was dissolved in 130 ml of water. The solution was adjusted to pH 6 with acetic acid. The precipitate was filtered, washed with water and dried to give 24 g (yield: 95.3%) of crystals, MP 97° to 98°C. Recrystallization from ligroin gave 1-(4'-methyl-6'-methoxy-2'-pyrimidinyl)-3-methyl-3-pyrazoline-5-one, MP 102° to 103°C.
To a solution of 4.76 g of 1-( 4'-methyl-6'-methoxy-2'-pyrimidinyl)-3-methyl- 3-pyrazoline 5-one in 200 ml of ether was added an ether solution containing 6 molar equivalents of diazomethane and the reaction mixture was allowed to stand at room temperature for 20 hours. After distilling off the solvent, the residue was dissolved in 160 ml of water, made alkaline (pH 10) with sodium hydroxide solution and extracted three times with 140 ml of benzene. The extract was washed with a small amount of water, dried over sodium sulfate and evaporated to give a crystalline mass. Recrystallization from isopropylether gave 1-(4'-methyl-6'-methoxy-2'-pyrimidinyl)-3-methyl-5- methoxypyrazole (3.96 g, 84%) as color less prisms, MP 90° to 92°C.

Therapeutic Function

Antiinflammatory, Analgesic, Antipyretic

Epirizole(18694-40-1)Related Product Information

• Methylparaben
• Thiophanate-methyl
• Pirimiphos-methyl
• Methyl acrylate
• Methyl acetate
• Kresoxim-methyl
• Glipizide
• Pyrazinamide
• Bensulfuron methyl
• Sulfamerazine
• Tetramethylpyrazine
• Methyl
• Parathion-methyl
• 2-Amino-4-methoxypyrimidine
• 2-Amino-4-methoxy-6-methylpyrimidine
• 2-Amino-6-methyl-4-pyrimidinol
• Methyl bromide
• 1,3-Dimethyl-5-hydroxypyrazole