Ormetoprim

Base Information

• Chemical Name: Ormetoprim
• CAS No.: 6981-18-6
• Molecular Formula: C14H18N4O2
• Molecular Weight: 274.323
• Hs Code.: 29333990
• European Community (EC) Number: 230-246-6
• NSC Number: 95072
• UNII: M3EFS94984
• DSSTox Substance ID: DTXSID1046689
• Nikkaji Number: J9.643A
• Wikidata: Q27166391
• NCI Thesaurus Code: C76643
• ChEMBL ID: CHEMBL494760
• Mol file: 6981-18-6.mol

Synonyms:2,4-diamino-5-(6-methylveratryl)pyrimidine;ormetoprim

Chemical Property of Ormetoprim

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 231.0 to 235.0 °C
• Refractive Index: 1.609
• Boiling Point: 521.5 °C at 760 mmHg
• PKA: 7.11±0.10(Predicted)
• Flash Point: 269.2 °C
• PSA: 96.28000
• Density: 1.223 g/cm³
• LogP: 2.71980
• Storage Temp.: 0-6°C
• Solubility.: Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 274.14297583
• Heavy Atom Count: 20
• Complexity: 305

Purity/Quality:

99%min ^*data from raw suppliers

Ormetoprim ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1CC2=CN=C(N=C2N)N)OC)OC
• Uses: It is a potent and selective inhibitor of bacterial dihydrofolate reductase, the enzyme responsible for the NADPH-dependent reduction of 7,8-dihydrofolate to 5,6,7,8-tetrahydrofolate. Antibacterial. It is a potent and selective inhibitor of bacterial dihydrofolate reductase, the enzyme responsible for the NADPH-dependent reduction of 7,8-dihydrofolate to 5,6,7,8-tetrahydrofolate. Antibacterial.This compound is a contaminant of emerging concern (CECs).

Technology Process of Ormetoprim

There total 20 articles about Ormetoprim which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

guanidine carbonate (593-85-1,90332-86-8,3425-08-9) + C14H17NO3 (7520-75-4) → ormetoprim (6981-18-6)

Guidance literature:

C₁₄H₁₇NO₃; With sodium methylate; In N,N-dimethyl-formamide; at 110 ℃;

guanidine carbonate; In N,N-dimethyl-formamide; at 130 ℃; Temperature;

Reference yield: 81.0%

→ ormetoprim (6981-18-6)

Guidance literature:

Reference yield: 62.0%

1,2-dimethoxy-4-methylbenzene (494-99-5) + 2,4-diamino-5-methoxymethylpyrimidine (54236-98-5) → ormetoprim (6981-18-6)

Guidance literature:

With hydrogenchloride; In methanol; for 7.5h; Ambient temperature;

DOI:10.1021/jo00039a006

upstream raw materials:

2-(methoxymethylene)-3-methoxypropanenitrile

1,2-dimethoxy-4-methylbenzene

guanidine hydrochloride

4,5-dimethoxy-2-methyl-2'-(methoxymethyl)cinnamonitrile

Refernces

• 1、 -. "A process for preparing 5 - substituted benzyl - 2, 4 - diamino pyrimidine and its derivatives (by machine translation)". . . Retrieved 2018/01/11.
• 2、 -. "Methods of using diaminopyrimidine P2X3 and P2X2/3 receptor modulators for treatment of respiratory and gastrointestinal diseases". Page/Page column 83. . Retrieved 2010/11/26.