{2-[(E)-[(dimethylamino)methylidene]amino]-4-oxo-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-3-yl}methyl 2,2-dimethylpropanoate

• ChemBase ID: 176817
• Molecular Formular: C15H21N5O3
• Molecular Mass: 319.35894
• Monoisotopic Mass: 319.16443956
• SMILES: c1c2c([nH]c1)c(=O)n(c(n2)/N=C/N(C)C)COC(=O)C(C)(C)C
• Canonical SMILES: CN(/C=N/c1nc2cc[nH]c2c(=O)n1COC(=O)C(C)(C)C)C
• InChI: InChI=1S/C15H21N5O3/c1-15(2,3)13(22)23-9-20-12(21)11-10(6-7-16-11)18-14(20)17-8-19(4)5/h6-8,16H,9H2,1-5H3/b17-8+
• InChIKey: TXSDMMQNNZXCGH-CAOOACKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-[(E)-[(dimethylamino)methylidene]amino]-4-oxo-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-3-yl}methyl 2,2-dimethylpropanoate
• IUPAC Traditional name: {2-[(E)-[(dimethylamino)methylidene]amino]-4-oxo-5H-pyrrolo[3,2-d]pyrimidin-3-yl}methyl 2,2-dimethylpropanoate
• Synonyms: 2,2-Dimethyl-propanoic Acid [2-[[(Dimethylamino)methylene]amino]-4,5-dihydro-4-oxo-3H-pyrrolo[3,2-d]pyrimidin-3-yl]methyl Ester; N1-(Pivaloyloxy)methyl-N2-(dimethylamino)methylene 9-Deazaguanine

Database IDs

• CAS Number: 151587-58-5
• PubChem SID: 164232727
• PubChem CID: 11758985

CALCULATED PROPERTIES

• Acid pKa: 11.730488
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.08271156
• LogD (pH = 7.4): 1.3422283
• Log P: 1.4876369
• Molar Refractivity: 86.8792 cm^3
• Polarizability: 31.96777 Å^3
• Polar Surface Area: 90.36 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Yellow Powder

DETAILS

Toronto Research Chemicals - P550770

9-Deazaguanosine intermendiate.

REFERENCES

• Semeraro, T., et al.: J. Med. Chem., 49, 6037 (2006)
• Hikishima, S., et al.: Bioorg. Med. Chem., 18, 2275 (2006)