[4-amino-2-(methylsulfanyl)pyrimidin-5-yl]methanol

• ChemBase ID: 65750
• Molecular Formular: C6H9N3OS
• Molecular Mass: 171.22016
• Monoisotopic Mass: 171.04663292
• SMILES: n1c(nc(c(c1)CO)N)SC
• Canonical SMILES: CSc1ncc(c(n1)N)CO
• InChI: InChI=1S/C6H9N3OS/c1-11-6-8-2-4(3-10)5(7)9-6/h2,10H,3H2,1H3,(H2,7,8,9)
• InChIKey: XLVOWGDFXAVSFE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [4-amino-2-(methylsulfanyl)pyrimidin-5-yl]methanol
• IUPAC Traditional name: [4-amino-2-(methylsulfanyl)pyrimidin-5-yl]methanol
• Synonyms: 4-Amino-2-(methylthio)-5-pyrimidinecarboxaldehyde; 4-Amino-2-methylsulfanylpyrimidine-5-carboxaldehyde; NSC 165376; 4-Amino-2-(methylthio)pyrimidine-5-carboxaldehyde; 4-Amino-2-methylthio-5-pyrimidinemethanol; (4-Amino-2-methanethiopyrimidin-5-yl)methanol; 2-Methylmercapto-4-amino-5-hydroxymethylpyrimidine; 4-Amino-2-methylmercapto-5-pyrimidinemethanol; NSC 3431; NSC 43811; Methioprim; 4-Amino-5-hydroxymethyl-2-(methylthio)pyrimidine; (4-Amino-2-(methylthio)pyrimidin-5-yl)methanol

Database IDs

• CAS Number: 770-31-0; 588-36-3
• MDL Number: MFCD08236793
• PubChem SID: 162031489
• PubChem CID: 220531

CALCULATED PROPERTIES

• Acid pKa: 14.34856
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.109166004
• LogD (pH = 7.4): 0.3506689
• Log P: 0.35492042
• Molar Refractivity: 47.257 cm^3
• Polarizability: 17.078047 Å^3
• Polar Surface Area: 72.03 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 97%; 98%

DETAILS

Toronto Research Chemicals - M260520

An intermediate used in the synthesis of Thiamine (T344185). Also, used for the preparation of pyridopyrimidines and naphthyridines as inhibitors of Akt kinase for the treatment of cancer.

Toronto Research Chemicals - A618265

Used for the preparation of pyridopyrimidines and naphthyridines as inhibitors of Akt kinase for the treatment of cancer.

REFERENCES

• Zinda, M., et al.: Clin. Cancer Res., 7, 2475 (2001)
• Breitenlechner, C., et al.: J. Med. Chem., 47, 1375 (2001)
• Zhao, Z., et al.: Bioorg. Med. Chem. Lett., 18, 49 (2001)
• Zinda, M., et al.: Clin. Cancer Res., 7, 2475 (2001)
• Breitenlechner, C., et al.: J. Med. Chem., 47, 1375 (2001)
• Zhao, Z., et al.: Bioorg. Med. Chem. Lett., 18, 49 (2001)