4-(1H-Pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine Chemical Properties

Boiling point:

501.8±50.0 °C(Predicted)

Density 

1.20±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

10.87±0.50(Predicted)

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

SMILES

C1=NC(C2=CNN=C2)=C2C=CN(COCC[Si](C)(C)C)C2=N1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HazardClass 

IRRITANT

4-(1H-Pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine Usage And Synthesis

Uses

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.

Synthesis

To a flask equipped was added 4-chloro-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine and dioxane and then added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole followed by a solution of potassium carbonate in water. The solution was degassed by passing a stream of nitrogen through the solution for 15 minutes before being treated with tetrakis(triphenylphosphine)palladium(0), and the resulting reaction mixture was heated at reflux (about 90° C) for 2 hours. When the reaction was complete, the mixture was cooled to room temperature and diluted with ethyl acetate and water. The two layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate (Na2SO4), and concentrated under reduced pressure. The residue was suspended in toluene, and the solvent was removed under reduced pressure. The residue was finally triturated with methyl tert-butyl ether, and the solid was collected by filtration and washed with MTBE to afford 4-(1H-pyrazol-4-yl)-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine (yield 64%) as white crystalline solids.

4-(1H-Pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine(941685-27-4)Related Product Information

• 4-(1H-Pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidine
• Baricitinib trifluoroacetate
• (4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate
• [4-(1H-Pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]methyl pivalate
• 2-(1-(ethylsulfonyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile
• 1H-Pyrazole-1-propanenitrile, β-cyclopentyl-4-[7-[[2-(triMethylsilyl)ethoxy]Methyl]-7H-pyrrolo[2,3-d]pyriMidin-4-yl]-
• 1H-Pyrazole-1-propanoic acid, β-cyclopentyl-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-, (βR)-
• 1H-Pyrazole-1-propanamide, β-cyclopentyl-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-, (βR)-
• 1H-Pyrazole-1-propanenitrile, β-cyclopentyl-4-[7-(hydroxyMethyl)-7H-pyrrolo[2,3-d]pyriMidin-4-yl]-,(βR)-
• 1H-Pyrazole-1-propanenitrile, β-(2-hydroxycyclopentyl)-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-, (βR)-
• 1H-Pyrazole-1-propanenitrile, 4-(6-amino-5-formyl-4-pyrimidinyl)-β-cyclopentyl-, (βR)-
• 1-(1-ethoxyethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
• Baricitinib
• 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile
• 4-(1-(1-ethoxyethyl)-1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine
• 1H-Pyrazole-1-propanamide, β-cyclopentyl-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-
• S-Ruxolitinib (INCB018424)
• 3-(4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile