5-(3,4-dichlorophenyl)-6-methylpyrimidine-2,4-diamine

• ChemBase ID: 4215
• Molecular Formular: C11H10Cl2N4
• Molecular Mass: 269.1299
• Monoisotopic Mass: 268.0282517
• SMILES: n1c(nc(c(c1C)c1cc(c(cc1)Cl)Cl)N)N
• Canonical SMILES: Nc1nc(C)c(c(n1)N)c1ccc(c(c1)Cl)Cl
• InChI: InChI=1S/C11H10Cl2N4/c1-5-9(10(14)17-11(15)16-5)6-2-3-7(12)8(13)4-6/h2-4H,1H3,(H4,14,15,16,17)
• InChIKey: VQJHOPSWBGJHQS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(3,4-dichlorophenyl)-6-methylpyrimidine-2,4-diamine
• IUPAC Traditional name: metoprine, methodichlorophen
• Synonyms: METOPRINE, METHODICHLOROPHEN; 5-(3,4-Dichlorophenyl)-6-methyl-2,4-pyrimidinediamine; 2,4-Diamino-5-(3,4-dichlorophenyl)-6-methylpyrimidine; 2,4-Diamino-5-(3',4'-dichlorophenyl)-6-methylpyrimidine; BW 197U; BW 50197; DDMP; Methodichlorophen; NSC 19494; NSC 7364; SK 5265; U 197; Metoprine

Database IDs

• CAS Number: 7761-45-7
• PubChem SID: 46504679; 160967647
• PubChem CID: 24466

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.210459
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.8319038
• LogD (pH = 7.4): 2.0226054
• Log P: 2.651812
• Molar Refractivity: 71.7199 cm^3
• Polarizability: 27.290316 Å^3
• Polar Surface Area: 77.82 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.87
• LOG S: -3.55
• Solubility (Water): 7.58e-02 g/l

DETAILS

DrugBank - DB04655

Drug information: experimental

Toronto Research Chemicals - M338835

A 2,4-Diaminopyrimidine derivative as antimalarial agent.

REFERENCES

• Andersson, K.J.I., et al.: Nature, 143, 720 (1939)
• Cecil, R., et al.: Biochem.J., et al.: 43, 592 (1939)