4-(1H-PYRAZOL-4-YL)-7-((2-(TRIMETHYLSILYL)ETHOXY)METHYL)-7H-PYRROLO[2,3-D]PYRIMIDINE

Base Information

• Chemical Name: 4-(1H-PYRAZOL-4-YL)-7-((2-(TRIMETHYLSILYL)ETHOXY)METHYL)-7H-PYRROLO[2,3-D]PYRIMIDINE
• CAS No.: 941685-27-4
• Molecular Formula: C15H21N5OSi
• Molecular Weight: 315.45
• Hs Code.: 2933990090
• Mol file: 941685-27-4.mol

Synonyms:4-(1H-Pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine;4-(1H-pyrazol-4-yl)-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine;

Chemical Property of 4-(1H-PYRAZOL-4-YL)-7-((2-(TRIMETHYLSILYL)ETHOXY)METHYL)-7H-PYRROLO[2,3-D]PYRIMIDINE

Chemical Property:

• Boiling Point: 501.8±50.0 °C(Predicted)
• PKA: 10.87±0.50(Predicted)
• PSA: 68.62000
• Density: 1.20±0.1 g/cm3(Predicted)
• LogP: 3.13370
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

4-(1H-Pyrazol-4-yl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of 4-(1H-PYRAZOL-4-YL)-7-((2-(TRIMETHYLSILYL)ETHOXY)METHYL)-7H-PYRROLO[2,3-D]PYRIMIDINE

There total 19 articles about 4-(1H-PYRAZOL-4-YL)-7-((2-(TRIMETHYLSILYL)ETHOXY)METHYL)-7H-PYRROLO[2,3-D]PYRIMIDINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.4%

7-((2-(trimethylsilyl)ethoxy)methyl)-4-(1H-3-chloropyrazol-4-yl)pyrrolo[2,3-d]pyrimidine → 4-(1H-pyrazol-4-yl)-7-((2-trimethylsilanylethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (941685-27-4)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; potassium carbonate; In tetrahydrofuran; at 50 - 55 ℃; for 5h; under 375.038 - 750.075 Torr; Reagent/catalyst; Solvent; Autoclave; Green chemistry;

Reference yield: 90.0%

4-(1-(1-ethoxyethyl)-1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (1187595-88-5) → 4-(1H-pyrazol-4-yl)-7-((2-trimethylsilanylethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (941685-27-4)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 8h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b00678

Reference yield: 88.0%

(3S)-3-cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (941685-41-2) → 4-(1H-pyrazol-4-yl)-7-((2-trimethylsilanylethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (941685-27-4)

Guidance literature:

potassium tert-butylate; In tetrahydrofuran; acetonitrile; at 0 - 20 ℃; Inert atmosphere;

upstream raw materials:

4-(1-(1-ethoxyethyl)-1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

pyrazole-4-boronic acid pinacol ester

4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

(3S)-3-cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile

Downstream raw materials:

2-(1-{1-[3-fluoro-2-(trifluoromethyl)pyridine-4-carbonyl]piperidin-4-yl}-3-(4-{7H-pyrrolo[2,3-d]pyrimidin-4-yl}-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile

2-(3-(4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-1-(1-(3-fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-yl)azetidin-3-yl)acetonitrile adipate

ruxolitinib

(3S)-3-cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile

Refernces

• 1、 -. "Simple synthetic method of 7-protecting group-4-(1-hydrogen-pyrazole-4-yl)pyrrole[2,3-d]pyrimidine". . . Retrieved 2019/04/30.
• 2、 Yao, Lianbin,Mustafa, Nurulhuda,Tan, Eng Chong,Poulsen, Anders,Singh, Prachi,Duong-Thi, Minh-Dao,Lee, Jeannie X. T.,Ramanujulu, Pondy Murugappan,Chng, Wee Joo,Yen, Jeffrey J. Y.,Ohlson, Sten,Dymock, Brian W.. "Design and Synthesis of Ligand Efficient Dual Inhibitors of Janus Kinase (JAK) and Histone Deacetylase (HDAC) Based on Ruxolitinib and Vorinostat". supporting information. p. 8336 - 8357. Retrieved 2017/11/03.