1144080-41-0

Upstream product

• 1144080-39-6 6-(4-nitrophenyl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol 
• 1144080-37-4 N-[4-cyano-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl]-4-nitrobenzamide 

Downstream Products

• 1144080-43-2 C₁₉H₁₇F₃N₆O₃ 
• 1174766-17-6 tert-butyl {4-[4-chloro-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}carbamate 

Relevant academic research and scientific papers

Convenient and practical one-pot synthesis of 4-chloropyrimidines via a novel chloroimidate annulation

Reaction of aromatic or heteroaromatic 2-acyl(amino)nitriles with phosphorus pentachloride triggers a novel chloroimidate cyclization, leading directly to the corresponding annullated 4-chloropyrimidines in good to excellent yields. The reaction lends itself to the telescoped one-pot construction of 4-functionalized pyrimidines from the corresponding (hetero)aromatic 2-aminonitriles. For a pyrazolopyrimidine development intermediate, this reaction was scaled up to multikilogram scale with excellent results. A total of 10 examples with different substrates are provided. This one-pot reaction provides an attractive and sustainable alternative to the commonly used multistep methodology for this transformation.

Discovery of 3,6-dihydro-2H-pyran as a morpholine replacement in 6-aryl-1H-pyrazolo[3,4-d]pyrimidines and 2-arylthieno[3,2-d]pyrimidines: ATP-competitive inhibitors of the mammalian target of rapamycin (mTOR)

The morpholine hinge-region binding group on a series of pyrazolopyrimidine and thienopyrimidine mammalian target of rapamycin (mTOR) inhibitors was replaced with 3,6-dihydro-2H-pyran (DHP), giving compounds of equivalent potency and selectivity versus PI3K. These results establish the DHP group as a hinge-region binding motif for the preparation of highly potent and selective mTOR inhibitors.

1H-PYRAZOLO[3,4-D]PYRIMIDINE, PURINE, 7H-PURIN-8(9H)-ONE, 3H-[1,2,3]TRIAZOLO[4,5-D]PYRIMIDINE, AND THIENO[3,2-D]PYRIMIDINE COMPOUNDS, THEIR USE AS mTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESES

The invention relates to 1H-pyrazolo[3,4-d]pyrimidine, purine, 7H-purin-8(9H)-one, 3H-[1,2,3]triazolo[4,5-d]pyrimidine, and thieno[3,2-d]pyrimidine compounds, compositions comprising the compounds, and methods for making and using the compounds.

Incorporation of water-solubilizing groups in pyrazolopyrimidine mTOR inhibitors: Discovery of highly potent and selective analogs with improved human microsomal stability

A series of highly potent and selective pyrazolopyrimidine mTOR inhibitors which contain water-solubilizing groups attached to the 6-arylureidophenyl moiety have been prepared. Such derivatives displayed superior potency to those in which these appendages