92440-76-1

Basic information

• Product Name: 2-amino-5-[(3,4,5-trimethoxyphenyl)methyl]-1H-pyrimidin-4-one
• Synonyms: 2-amino-5-[(3,4,5-trimethoxyphenyl)methyl]-1H-pyrimidin-4-one;2-Amino-5-[(3,4,5-trimethoxyphenyl)methyl]-4(1H)-pyrimidinone;5-(3,4,5-Trimethoxybenzyl)-2-aminopyrimidin-4-ol;2-AMino-5-(3,4,5-triMethoxybenzyl)-4-pyriMidinol;Trimethoprim EP Impurity D
• CAS NO: 92440-76-1
• Molecular Formula: C₁₄H₁₇N₃O₄
• Molecular Weight: 291.30248
• EINECS: 296-233-2
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 92440-76-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 257-258 °C(Solv: ethanol, 50% (64-17-5))
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.31g/cm³
• Refractive Index: 1.587
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.40±0.50(Predicted)
• CAS DataBase Reference: 2-amino-5-[(3,4,5-trimethoxyphenyl)methyl]-1H-pyrimidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-5-[(3,4,5-trimethoxyphenyl)methyl]-1H-pyrimidin-4-one(92440-76-1)
• EPA Substance Registry System: 2-amino-5-[(3,4,5-trimethoxyphenyl)methyl]-1H-pyrimidin-4-one(92440-76-1)

Safety Data

• Hazardous Substances Data: 92440-76-1(Hazardous Substances Data)

Usage

Uses

Degradation product/impurity of trimethoprim (T795615).

InChI:InChI=1/C14H17N3O4/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-16-14(15)17-13(9)18/h5-7H,4H2,1-3H3,(H3,15,16,17,18)

Upstream product

• 738-70-5 5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine 
• 70311-20-5 3-(3,4,5-trimethoxyphenyl)propionic acid ethyl ester 
• 593-85-1 diguanidine carbonate 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 55694-04-7 2-amino-4-chloro-5-(3,4,5-trimethoxybenzyl)pyrimidine 
• 92653-78-6 2-amino-4-methylamino-5-(3,4,5-trimethoxybenzyl)pyrimidine 

Relevant articles and documents

Separation, analyses and syntheses of trimethoprim impurities

The analysis of several impurities of the chemotherapeutic agent trimethoprim with various methods, including thin layer chromatography, gas chromatography, capillary electrophoresis as well as nuclear magnetic resonance is described. These methods were used to identify new impurities in trimethoprim batches. The main impurities were separated by column chromatography. To ensure the identity of the impurities, de novo syntheses were successfully carried out. With the methods described, it was possible to detect, separate and identify new impurities in trimethoprim batches.

Degradation of trimethoprim

Trimethoprim undergoes thermally and photochemically catalyzed hydrolysis or oxidation to give rise to at least five products. The structures of these compounds were determined by physical methods and it was found that the resonance of C-5 in the 13C NMR spectrum is indicative of the substitution pattern of the resultant amino hydroxy pyrimidines.