78727-16-9

Basic information

• Product Name: N-METHYL-7H-PYRROLO[2,3-D]PYRIMIDIN-4-AMINE
• Synonyms: N-METHYL-7H-PYRROLO[2,3-D]PYRIMIDIN-4-AMINE;7H-Pyrrolo[2,3-d]pyrimidin-4-amine, N-methyl- (9CI)
• CAS NO: 78727-16-9
• Molecular Formula: C₇H₈N₄
• Molecular Weight: 148.17
• Product Categories: PYRIMIDINE
• Mol File: 78727-16-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 235 °C
• Boiling Point: 323.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.39±0.1 g/cm3(Predicted)
• PKA: 13.56±0.20(Predicted)
• CAS DataBase Reference: N-METHYL-7H-PYRROLO[2,3-D]PYRIMIDIN-4-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-METHYL-7H-PYRROLO[2,3-D]PYRIMIDIN-4-AMINE(78727-16-9)
• EPA Substance Registry System: N-METHYL-7H-PYRROLO[2,3-D]PYRIMIDIN-4-AMINE(78727-16-9)

Safety Data

• Hazardous Substances Data: 78727-16-9(Hazardous Substances Data)

Usage

General Description

N-Methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine is a chemical compound with the molecular formula C8H8N4. It is a derivative of pyrrolopyrimidine, which is a heterocyclic compound containing both a pyrrole and a pyrimidine ring. N-METHYL-7H-PYRROLO[2,3-D]PYRIMIDIN-4-AMINE has a methyl group attached to the nitrogen atom, and an amine group attached to the 4-position of the pyrimidine ring. It may have potential applications in pharmaceutical research, particularly in the development of new drugs targeting specific biological pathways or processes. Further research is needed to fully understand the properties and potential uses of N-Methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine.

Upstream product

• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 74-89-5 methylamine 
• 1500-85-2 7-deazaadenine 
• 50-00-0 formaldehyd 
• 910789-32-1 methyl-[7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine 
• 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 articles and documents

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).

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.

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.