ChemicalBook CAS DataBase List 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 synthesis

10synthesis methods

Product Name:4-(1H-Pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine
CAS Number:941685-27-4
Molecular formula:C15H21N5OSi
Molecular Weight:315.45

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. Also used For Barretinib Barretinib intermediate. Its synthesis is shown below： Pyrazole-4-boronic acid pinacol ester and 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine with potassium carbonate in water Reaction at room temperature, catalyzed by tetrakis(triphenylphosphine) palladium(0) for 2h to obtain 4-(1H-Pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl-7H-pyrrolo[2,3-d]pyrimidine.

269410-08-4 Synthesis

269410-08-4
380 suppliers
$5.00/1g

941685-26-3 Synthesis

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

941685-26-3
166 suppliers
$59.00/250mg

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

941685-27-4
229 suppliers
$18.00/250mg

Yield:941685-27-4 166.4 g

Reaction Conditions:

Stage #1:pyrazole-4-boronic acid pinacol ester;4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine with potassium carbonate in water at 25 - 30;Inert atmosphere;
Stage #2: with tetrakis(triphenylphosphine) palladium⁽⁰⁾ at 78 - 80; for 2 h;Inert atmosphere;

Steps:

1.b Preparation of 4-(lH-pyrazol-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H- pyr rolo [2,3-d] pyrimidine
Nitrogen gas was purged through a mixture of 4-chloro-7- { [2- (0224) (trimemylsilyl)ethoxy]memyl}-7H-pyIτolo[2,3-

References:

SUN PHARMACEUTICAL INDUSTRIES LIMITED;CHAWLA, Deepshikha;BARMAN, Dhiren, Chandra;CHATTERJEE, Pranab;NATH, Asok;PRASAD, Mohan WO2016/35014, 2016, A1 Location in patent:Page/Page column 27

941685-41-2 Synthesis