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

• ChemBase ID: 157532
• Molecular Formular: C14H18N4O3
• Molecular Mass: 290.31772
• Monoisotopic Mass: 290.13789046
• SMILES: COc1cc(cc(c1OC)OC)Cc1cnc(nc1N)N
• Canonical SMILES: COc1cc(Cc2cnc(nc2N)N)cc(c1OC)OC
• InChI: InChI=1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18)
• InChIKey: IEDVJHCEMCRBQM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{[3,4,5-tris(^2H₃)methoxyphenyl]methyl}pyrimidine-2,4-diamine
• IUPAC Traditional name: 5-{[3,4,5-tris(^2H₃)methoxyphenyl]methyl}pyrimidine-2,4-diamine
• Synonyms: 2,4-Diamino-5-(3,4,5-tri(methoxy-d3)benzyl)pyrimidine; Trimethoprim-d9; 5-[(3,4,5-Trimethoxy-d9-phenyl)methyl]-2,4-pyrimidinediamine; 2,4-Diamino-5-(3',4',5'-trimethoxy-d9-benzyl)pyrimidine; Instalac-d9; Monotrim-d9; Proloprim-d9; Syraprim-d9; Tiempe-d9; Trimanyl-d9; Uretrim-d9; Wellcoprim-d9; Trimethoprim-d9 (Major); 2,4-二氨基-5-(3,4,5-三(甲氧基-d3)苄基)嘧啶; 甲氧苄啶-d9

Database IDs

• CAS Number: 1189460-62-5
• MDL Number: MFCD09841385
• PubChem SID: 162251669
• PubChem CID: 45040631

CALCULATED PROPERTIES

• Acid pKa: 17.334406
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.020083463
• LogD (pH = 7.4): 1.0960962
• Log P: 1.2839073
• Molar Refractivity: 81.5094 cm^3
• Polarizability: 29.762405 Å^3
• Polar Surface Area: 105.51 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 207-212°C
• Mass Shift: M+9

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Temperature Sensitive
• German water hazard class: 3

Product Information

• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C14D9H9N4O3

DETAILS

Sigma Aldrich - 32414

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

Toronto Research Chemicals - T795617

Deuterated Trimethoprim, an antibacterial.contains 90% D9, 10% D6 and no D0

REFERENCES

• Manius, G.J., et al.: Anal. Profiles Drug Subs., 7, 445 (1978)
• Roth, B., et al.: J. Med. Chem., 23, 379 (1978)
• Brogden, R.N., et al.: Drugs, 23, 405 (1978)