4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazole

• ChemBase ID: 32564
• Molecular Formular: C15H21N5OSi
• Molecular Mass: 315.44564
• Monoisotopic Mass: 315.15153685
• SMILES: n1cnc2c(c1c1c[nH]nc1)ccn2COCC[Si](C)(C)C
• Canonical SMILES: C[Si](CCOCn1ccc2c1ncnc2c1c[nH]nc1)(C)C
• InChI: InChI=1S/C15H21N5OSi/c1-22(2,3)7-6-21-11-20-5-4-13-14(12-8-18-19-9-12)16-10-17-15(13)20/h4-5,8-10H,6-7,11H2,1-3H3,(H,18,19)
• InChIKey: AVMLPTWVYQXRSV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazole
• IUPAC Traditional name: 4-(7-{[2-(trimethylsilyl)ethoxy]methyl}pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazole
• Synonyms: 4-(1H-Pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)-methyl)-7H-pyrrolo[2,3-d]pyrimidine; 4-(1H-Pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine; INCB032304; 4-(1H-Pyrazol-4-yl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine; 4-(1H-Pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

Database IDs

• CAS Number: 941685-27-4
• MDL Number: MFCD11857754
• PubChem SID: 160995871
• PubChem CID: 42631346

CALCULATED PROPERTIES

• Acid pKa: 13.284107
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.922144
• LogD (pH = 7.4): 3.1431925
• Log P: 3.1469
• Molar Refractivity: 83.3933 cm^3
• Polarizability: 35.528275 Å^3
• Polar Surface Area: 68.62 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Empirical Formula (Hill Notation): C15H21N5OSi

DETAILS

Sigma Aldrich - ADE001297

Other Notes
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Legal Information
Product of Adesis

Toronto Research Chemicals - P847000

4-(1H-Pyrazol-4-yl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine is an important intermediate in the preparation of the janus kinase inhibitor INCB018424.

REFERENCES

• Lin, Q. et al.: Org. Lett., 11, 1999 (2009)