78727-16-9

Usage

Uses

Used in Pharmaceutical Research:
N-METHYL-7H-PYRROLO[2,3-D]PYRIMIDIN-4-AMINE is used as a chemical intermediate for the development of new drugs. Its unique structure allows it to potentially target specific biological pathways or processes, making it a valuable candidate for drug discovery and design.
Used in Drug Development:
In the pharmaceutical industry, N-METHYL-7H-PYRROLO[2,3-D]PYRIMIDIN-4-AMINE is used as a building block for the synthesis of novel compounds with potential therapeutic applications. Its heterocyclic nature and functional groups may contribute to the creation of drugs with improved efficacy, selectivity, and safety profiles.

Upstream product

• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 74-89-5 methylamine 
• 910789-32-1 methyl-[7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine 
• 50-00-0 formaldehyd 
• 1500-85-2 7-deazaadenine 
• 78727-12-5 4-Amino-3-methylpyrrolo<2,3-d>pyrimidin-hydrochlorid 

Downstream Products

• 1259404-17-5 tasocitinib 
• 910789-32-1 methyl-[7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine 
• 540737-29-9 Tofacitinib citrate 
• 477600-74-1 tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate 
• 125417-81-4 7-<2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl>-4-(methylamino)-1H-pyrrolo<2,3-d>pyrimidine 
• 125417-68-7 7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-4-(methylamino)-7H-pyrrolo<2,3-d>pyrimidine 

Relevant academic research and scientific papers

N6-modification of 7-Deazapurine nucleoside analogues as Anti-Trypanosoma cruzi and anti-Leishmania agents: Structure-activity relationship exploration and In vivo evaluation

Chagas disease and leishmaniasis are two poverty-related neglected tropical diseases that cause high mortality and morbidity. Current treatments suffer from severe limitations and novel, safer and more effective drugs are urgently needed. Both Trypanosoma cruzi and Leishmania are auxotrophic for purines and absolutely depend on uptake and assimilation of host purines. This led us to successfully explore purine nucleoside analogues as chemotherapeutic agents against these and other kinetoplastid infections. This study extensively explored the modification of the 6-amino group of tubercidin, a natural product with trypanocidal activity but unacceptable toxicity for clinical use. We found that mono-substitution of the amine with short alkyls elicits potent and selective antitrypanosomal and antileishmanial activity. The methyl analogue 15 displayed the best in vitro activity against both T. cruzi and L. infantum and high selectivity versus host cells. Oral administration for five consecutive days in an acute Chagas disease mouse model resulted in significantly reduced peak parasitemia levels (75, 89 and 96% with 12.5, 25 and 50 mg/kg/day, respectively). as well as increased animal survival rates with the lower doses (83 and 67% for 12.5 and 25 mg/kg/day, respectively).

Short enantioselective total synthesis of (+)-tofacitinib

An enantioselective total synthesis of Tofacitinib (CP-690,550), a Janus tyrosine kinase (JAK3) specific inhibitor has been achieved from the readily available 4-piperidone. Proline catalysed hydroxylation is the key step for the synthesis of enantiopure 1-benzyl-4-methylpiperidin-3-ol.

Asymmetric total synthesis of Tofacitinib

A novel stereoselective synthesis of Tofacitinib (CP-690,550), a Janus tyrosine kinase (JAK3) specific inhibitor, has been achieved starting from (5S)-5-hydroxypiperidin-2-one in 10 steps from 2 with a 9.5% overall yield. The potentiality of this synthetic route is the obtention of tert-butyl-(3S,4R)-3- hydroxy-4-methylpiperidine-1-carboxylate (6b) as a new chiral precursor involved in the synthesis of CP690,550, in a three-step reaction, without epimerizations, rather than the 5 or more steps used in described reactions to achieve this compound from analogues of 6b.

Bis-aryl urea compounds and methods of use

The present invention relates to compounds of Formulas I and II, wherein A1, A2, B1, B2, Q, X1, X2, Y and R3 are defined herein, synthetic intermediates, and pharmaceutical compositions, comprising such compounds. The compounds and compositions are capable of modulating various protein kinase receptors such as Tie-2 and, therefore, influencing kinase related disease states and conditions. The compounds, for example, are capable of treating cancer caused by unregulated angiogenesis, and inflammation as well as other proliferative disorders.

Deprotection of N-tosylated indoles and related structures using cesium carbonate

A very mild, efficient, and convenient method for deprotection of N-tosylated indoles and related structures by cesium carbonate in THF-MeOH is described.

The Isomeric 4-Amino-N-methylpyrrolopyrimidines

Methylation of 4-amino-7H-pyrrolopyrimidine (2a) (neutral conditions) leads to a 1:1 mixture of N-1 (6a) and N-3 isomers (5a).The structural assignment was accomplished by Dimroth rearrangement of 5a yielding 2e.The isomer 6a is also obtained by de