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

• ChemBase ID: 121657
• Molecular Formular: C13H16N4O2
• Molecular Mass: 260.29174
• Monoisotopic Mass: 260.12732577
• SMILES: n1c(c(cnc1N)Cc1cc(c(cc1)OC)OC)N
• Canonical SMILES: COc1cc(ccc1OC)Cc1cnc(nc1N)N
• InChI: InChI=1S/C13H16N4O2/c1-18-10-4-3-8(6-11(10)19-2)5-9-7-16-13(15)17-12(9)14/h3-4,6-7H,5H2,1-2H3,(H4,14,15,16,17)
• InChIKey: LDBTVAXGKYIFHO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(3,4-dimethoxyphenyl)methyl]pyrimidine-2,4-diamine
• IUPAC Traditional name: diaveridine; 5-[(3,4-dimethoxyphenyl)methyl]pyrimidine-2,4-diamine
• Synonyms: 5-(3,4-dimethoxybenzyl)pyrimidine-2,4-diamine; 5-(3,4-Dimethoxybenzyl)-2,4-pyrimidinediamine; Diaveridine; 5-(3,4-二甲氧基苄基)-2,4-嘧啶二胺; 敌菌净

Database IDs

• CAS Number: 5355-16-8
• EC Number: 226-333-3
• MDL Number: MFCD00057349
• Beilstein Number: 258464
• PubChem SID: 24894302; 24869907; 162216010
• PubChem CID: 21453

CALCULATED PROPERTIES

• Acid pKa: 17.339434
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.17743787
• LogD (pH = 7.4): 1.2534758
• Log P: 1.4415786
• Molar Refractivity: 75.0462 cm^3
• Polarizability: 27.220407 Å^3
• Polar Surface Area: 96.28 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: UV8142000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: rat ... Dhfr(24312)

Product Information

• Purity: ≥99.0% (TLC)
• Grade: VETRANAL™, analytical standard
• Application(s): Analgesic; Anthelmintic; Antibacterial; Antiinflammatory; Antiprotozoal; Antipyretic
• Empirical Formula (Hill Notation): C13H16N4O2

DETAILS

Sigma Aldrich - 46174

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

REFERENCES

• Falco, E.A. et al., J.A.C.S., 1951, 73, 3758, (synth)
• Brossi, A. et al., J. Med. Chem., 1971, 14, 58; 462, (synth, pharmacol)
• Koetzle, T.F. et al., Acta Cryst. B, 1978, 34, 323, (struct)
• Blaney, J.M. et al., J. Med. Chem., 1979, 22, 614, (synth, props)
• Calas, M. et al., Eur. J. Med. Chem. (Chim. Ther.), 1982, 17, 497, (synth, props)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 511