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

• ChemBase ID: 179169
• Molecular Formular: C14H18N4O3
• Molecular Mass: 290.31772
• Monoisotopic Mass: 290.13789046
• SMILES: c1(c(c(cc(c1)Cc1c(nc(nc1)N)N)OC)OC)OC
• 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-{[4-(^2H₃)methoxy-3,5-dimethoxyphenyl]methyl}pyrimidine-2,4-diamine
• IUPAC Traditional name: 5-{[4-(^2H₃)methoxy-3,5-dimethoxyphenyl]methyl}pyrimidine-2,4-diamine
• Synonyms: 5-[(3,4,5-Trimethoxy-d3-phenyl)methyl]-2,4-pyrimidinediamine; 2,4-Diamino-5-(3',4',5'-trimethoxy-d3-benzyl)pyrimidine; Instalac-d3; Monotrim-d3; Proloprim-d3; Syraprim-d3; Tiempe-d3; Trimanyl-d3; Uretrim-d3; Wellcoprim-d3; Trimethoprim-d3

Database IDs

• CAS Number: 1189923-38-3
• PubChem SID: 164235079
• PubChem CID: 46783191

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: 29.760473 Å^3
• Polar Surface Area: 105.51 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 208-210°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T795618

Deuterated Trimethoprim, an antibacterial.

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)