ethyl 4-amino-2-(methylsulfanyl)pyrimidine-5-carboxylate

• ChemBase ID: 65749
• Molecular Formular: C8H11N3O2S
• Molecular Mass: 213.25684
• Monoisotopic Mass: 213.05719761
• SMILES: n1c(nc(c(c1)C(=O)OCC)N)SC
• Canonical SMILES: CCOC(=O)c1cnc(nc1N)SC
• InChI: InChI=1S/C8H11N3O2S/c1-3-13-7(12)5-4-10-8(14-2)11-6(5)9/h4H,3H2,1-2H3,(H2,9,10,11)
• InChIKey: QINRQIZOBCQKAZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-amino-2-(methylsulfanyl)pyrimidine-5-carboxylate
• IUPAC Traditional name: ethyl 4-amino-2-(methylsulfanyl)pyrimidine-5-carboxylate
• Synonyms: Ethyl 4-amino-2-(methylthio)-pyrimidine-5-carboxylate; 4-Amino-2-(methylsulphanyl)pyrimidine-5-carboxylic acid ethyl ester; Ethyl 4-amino-2-(methylthio)pyrimidine-5-carboxylate; Ethyl 4-amino-2-(methylthio)pyrimidine-5-carboxylate; Ethyl 4-amino-2-methylsulfanyl-5-pyrimidinecarboxylate; NSC 9310; 4-Amino-2-(methylthio)-5-pyrimidinecarboxylic Acid Ethyl Ester

Database IDs

• CAS Number: 776-53-4
• MDL Number: MFCD00090781
• PubChem SID: 162031488
• PubChem CID: 222666

CALCULATED PROPERTIES

• Acid pKa: 17.35398
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.1122632
• LogD (pH = 7.4): 2.1322932
• Log P: 2.132555
• Molar Refractivity: 57.215 cm^3
• Polarizability: 20.9153 Å^3
• Polar Surface Area: 78.1 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 134 - 136°C
• Hydrophobicity(logP): 2.19

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95%; 97%; 98%

DETAILS

Toronto Research Chemicals - A618240

Used for preparation of pyrimidopyrimidines as protein kinase inhibitors.

REFERENCES

• Schow, S., et al.: Bioorg. Med. Chem. Lett., 7, 2697 (1997)
• Zaharevitz, D., et al.: Cancer Res., 59, 2566 (1997)
• Dreyer, M., et al.: J. Med. Chem., 44, 524 (1997)