5-[(4-bromo-3,5-dimethoxyphenyl)methyl]pyrimidine-2,4-diamine

• ChemBase ID: 162711
• Molecular Formular: C13H15BrN4O2
• Molecular Mass: 339.1878
• Monoisotopic Mass: 338.03783774
• SMILES: c1(c(c(cc(c1)Cc1c(nc(nc1)N)N)OC)Br)OC
• Canonical SMILES: COc1cc(Cc2cnc(nc2N)N)cc(c1Br)OC
• InChI: InChI=1S/C13H15BrN4O2/c1-19-9-4-7(5-10(20-2)11(9)14)3-8-6-17-13(16)18-12(8)15/h4-6H,3H2,1-2H3,(H4,15,16,17,18)
• InChIKey: BFCRRLMMHNLSCP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(4-bromo-3,5-dimethoxyphenyl)methyl]pyrimidine-2,4-diamine
• IUPAC Traditional name: brodimoprim
• Synonyms: 5-[(4-Bromo-3,5-dimethoxyphenyl)methyl]-2,4-pyrimidinediamine; 5-(4-Bromo-3,5-dimethoxybenzyl)-2,4-pyrimidinediamine; Hyprim; Ro 10-5970; Ro 105970; Unitrim; Brodimoprim

Database IDs

• CAS Number: 56518-41-3
• PubChem SID: 162256846
• PubChem CID: 68760

CALCULATED PROPERTIES

• Acid pKa: 17.330223
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.94662917
• LogD (pH = 7.4): 2.022632
• Log P: 2.2103312
• Molar Refractivity: 82.669 cm^3
• Polarizability: 30.09227 Å^3
• Polar Surface Area: 96.28 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 228-230°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - B678100

A structural derivative of Trimethoprim (T795615). A selective dihydrofolate reductase inhibitor; diaminopyridine antibacterial agent.

REFERENCES

• Thomson, C.J. et al.: J. Chemother., 5, 458 (1993)
• Hawserl, S. et al.: Biochem. Pharmacol., 71, 941 (1993)
• Conforti, A. et al.: Br. J. Clin. Pharmacol., 44, 411 (1993)