5-{[3-bromo-4-(2H3)methoxy-5-methoxyphenyl]methyl}pyrimidine-2,4-diamine

• ChemBase ID: 166254
• Molecular Formular: C13H15BrN4O2
• Molecular Mass: 339.1878
• Monoisotopic Mass: 338.03783774
• SMILES: c1(c(c(cc(c1)Cc1c(nc(nc1)N)N)OC)OC)Br
• Canonical SMILES: COc1c(Br)cc(cc1OC)Cc1cnc(nc1N)N
• InChI: InChI=1S/C13H15BrN4O2/c1-19-10-5-7(4-9(14)11(10)20-2)3-8-6-17-13(16)18-12(8)15/h4-6H,3H2,1-2H3,(H4,15,16,17,18)
• InChIKey: XJSNBPJINGRLAM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{[3-bromo-4-(^2H₃)methoxy-5-methoxyphenyl]methyl}pyrimidine-2,4-diamine
• IUPAC Traditional name: 5-{[3-bromo-4-(^2H₃)methoxy-5-methoxyphenyl]methyl}pyrimidine-2,4-diamine
• Synonyms: 5-[[3-Bromo-4-(methoxy-d3)-5-methoxyphenyl]methyl]-2,4-diaminopyrimidine; 2,4-Diamino-5-(5-bromoveratryl)pyrimidine; 2,4-Diamino-5-[3-methoxy-4-(methoxy-d3)-5-bromobenzyl]pyrimidine; 2,4-Diamino-5-[3-bromo-4-(methoxy-d3)-5-methoxybenzyl]pyrimidine; 5-[3’-Bromo-4’-(methoxy-d3)-5’-methoxybenzyl]-2,4-diaminopyrimidine; 4-Desmethoxy-4-bromo Trimethoprim-d3

Database IDs

• PubChem SID: 162260387
• PubChem CID: 71315650

CALCULATED PROPERTIES

• Acid pKa: 17.337008
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.946331
• LogD (pH = 7.4): 2.022358
• Log P: 2.2103312
• Molar Refractivity: 82.669 cm^3
• Polarizability: 30.087158 Å^3
• Polar Surface Area: 96.28 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D290312

A labelled impurity of Trimethoprim (T795615) with inhibitory effects on the enzyme dihydrofolate reductase.

REFERENCES

• Kompis, I. et al.: Enzyme Inhib. Proc. Meet., 177 (1980)
• Hess, S. et al.: J. Pharmac. Biomed. Anal., 25, 531 (1980)