Ruxolitinib Impurity B CAS#: 1001070-45-6; ChemWhat Code: 1410845

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product NameRuxolitinib Impurity B
IUPAC Name7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine
Molecular StructureStructure of Ruxolitinib Impurity B CAS 1001070-45-6
CAS Registry Number 1001070-45-6
EINECS NumberNo data available
MDL NumberNo data available
Beilstein Registry NumberNo data available
Synonyms7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine;
7H-Pyrrolo[2,3-d]pyrimidine, 7-[[2-(trimethylsilyl)ethoxy]methyl]-;
Ruxolitinib Impurity 3
Molecular FormulaC12H19N3OSi
Molecular Weight249.388
InChINo data available
InChI KeyWUHSWAJJIXAIGL-UHFFFAOYSA-N
Canonical SMILESNo data available
Patent Information
No data available

Physical Data

AppearanceWhite powder
SolubilityNo data available
Flash PointNo data available
Refractive indexNo data available
SensitivityNo data available

Spectra

Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Temperature (NMR Spectroscopy), °C Frequency (NMR Spectroscopy), MHzOriginal Text (NMR Spectroscopy)
1Hchloroform-d126.84400
1
H-NMR (400 MHz, CDCl3): δ 9.1 (bs, 1H), 9.0 (bs, 1H), 7.43 (bd, J=4 Hz, 1H), 6.68 (bd, J=4 Hz, 1H), 5.73 (s, 1H), 3.6 (t, J=8 Hz, 2H), 0.97 (t, J=8 Hz, 2H), 0.1 (s, 9H)

Route of Synthesis (ROS)

Route of Synthesis (ROS) of Ruxolitinib Impurity B CAS 1001070-45-6
Route of Synthesis (ROS) of Ruxolitinib Impurity B CAS 1001070-45-6
ConditionsYield
Stage #1: 7H-pyrrolo[2,3-d]pyrimidine With sodium hydride In tetrahydrofuran at 0 – 20℃;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran at 20℃; for 2h;
Experimental Procedure
7H-Pyrrolo[2,3-d]pyrimidine (1.16 g, 9.74 mmol), was dissolved in 100 ml anhydrous THF under N2. At 0° C., a 60% dispersion of NaH 0.51 g in mineral oil was added. The mixture was stirred at ambient temperature and 2.93 ml (9.8 mmol) (2-chloromethoxy-ethyl)-trimethyl-silane dissolved in 15 ml anhydrous THF was added. The reaction mixture was stirred at room temperature for 2 hour and subsequently concentrated in vacuo. Ethyl acetate was added to the mixture and the organic layer was washed three times with a saturated NaHCO3 solution, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by flash chromatography (diethyl ether) to afford 7-(2-trimethylsilanyl-ethoxymethyl-7H-pyrrolo[2,3-d]pyrimidine (compound 91), (amorphous, 0.84 g, 35%). 1H-NMR (400 MHz, CDCl3): δ 9.1 (bs, 1H), 9.0 (bs, 1H), 7.43 (bd, J=4 Hz, 1H), 6.68 (bd, J=4 Hz, 1H), 5.73 (s, 1H), 3.6 (t, J=8 Hz, 2H), 0.97 (t, J=8 Hz, 2H), 0.1 (s, 9H).
35%

Safety and Hazards

GHS Hazard StatementsNo data available
For more detailed information, please visit ECHA C&L website

Source: European Chemicals Agency (ECHA)
License Note: Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: “Source: European Chemicals Agency, http://echa.europa.eu/”. Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
License URL: https://echa.europa.eu/web/guest/legal-notice
Record Name: (1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate
URL: https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/213446
Description: The information provided here is aggregated from the “Notified classification and labelling” from ECHA’s C&L Inventory. Read more: https://echa.europa.eu/information-on-chemicals/cl-inventory-database

Other Data

TransportationUnder the room temperature and away from light
HS CodeNo data available
StorageUnder the room temperature and away from light
Shelf Life2 years
Market PriceUSD
Druglikeness
Lipinski rules component
Molecular Weight249.388
logP2.698
HBA4
HBD0
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)39.94
Rotatable Bond (RotB)5
Matching Veber Rules2
Use Pattern
Ruxolitinib Impurity B CAS 1001070-45-6 used as the Impurity of Ruxolitinib.

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