173459-05-7

Basic information

• Product Name: 4-Chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine
• Synonyms: 4-Chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine
• CAS NO: 173459-05-7
• Molecular Weight: 229.669
• Mol File: 173459-05-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 402.8±55.0 °C(Predicted)
• Density: 1.40±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 4-Chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine(173459-05-7)
• EPA Substance Registry System: 4-Chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine(173459-05-7)

Safety Data

• Hazardous Substances Data: 173459-05-7(Hazardous Substances Data)

Upstream product

• 70-11-1 α-bromoacetophenone 
• 111222-40-3 ethyl 2-amino-5-phenyl-1H-pyrrole-3-carboxylate 
• 173458-99-6 6-Phenyl-4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine 

Downstream Products

• 417721-62-1 4-(4-Nitrophenoxy)-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine 
• 1590459-85-0 4-chloro-7-methyl-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine 
• 1418273-04-7 (S)-N-(1-(naphthalen-1-yl)ethyl)-6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1418273-03-6 (R)-N-(1-(naphthalen-1-yl)ethyl)-6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1350639-75-6 (R)-N-(1-(4-fluorophenyl)ethyl)-6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1222448-28-3 (R)-6-phenyl-N-(1-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1643962-24-6 (S)-N-(2-methoxy-1-phenylethyl)-6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1643962-22-4 (S)-2-phenyl-2-((6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethanol 
• 1610549-27-3 C₁₇H₁₆N₆S 
• 1610549-23-9 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-(5-{2-[(6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]ethyl}-1,3-thiazol-2-yl)urea 
• 1610549-22-8 1-(1,2-oxazol-3-yl)-3-(5-{2-[(6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]ethyl}-1,3-thiazol-2-yl)urea 
• 1610549-21-7 1-phenyl-3-(5-(2-(6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)ethyl)thiazol-2-yl)urea 
• 1610549-19-3 1-(3-chlorophenyl)-3-(5-(2-(6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)ethyl)thiazol-2-yl)urea 

Relevant articles and documents

4-AMINO-6-ARYL[2,3-D]PYRIMIDINES FOR THE INHIBITION OF EGFR TYROSINE KINASE

This invention relates to certain new pyrrolo-, thieno-, and furo-[2,3- d]pyrimidine compounds, such as of general formula (I) These compounds are epidermal growth factor receptor tyrosine kinase inhibitors and therefore offer potential in the treatment of cancer.

SUBSTITUTED HETERO-BICYCLIC COMPOUNDS, COMPOSITIONS AND MEDICINAL APPLICATIONS THEREOF

The present disclosure provides hetero-biclyclic compounds of formula (I), their tautomers, polymorphs, stereoisomers, prodrugs, solvates, hydrates, N-oxides, co-crystals, pharmaceutically acceptable salts, pharmaceutical compositions containing them and methods of treating conditions and diseases that are mediated by Bruton's tyrosine kinase (Btk) activity, The disclosure also relates to the process of preparation of compounds of Formula (I). These compounds are useful in the treatment, prevention, prophylaxis, management, or adjunct treatment of all medical conditions related to inhibition of Bruton's tyrosine kinase (Btk), such as inflammatory and/or autoimmune disorder, cell proliferation, rheumatoid arthritis, psoriasis, psoriatic arthritis, transplant rejection, graft-versus-host disease, multiple sclerosis, inflammatory bowel disease, allergic diseases, asthma, type 1 diabetes, myasthenia gravis, hematopoetic disfunction, B-cell malignancies, systemic lupus, erythematosus or other disorders.

Synthesis and in vitro EGFR (ErbB1) tyrosine kinase inhibitory activity of 4-N-substituted 6-aryl-7H-pyrrolo[2,3-d]pyrimidine-4-amines

A series of 4-N-substituted 6-aryl-7H-pyrrolo[2,3-d]pyrimidine-4-amines have been synthesised, characterised and tested for their in vitro EGFR (ErbB1) tyrosine kinase inhibitory activity. The compounds were prepared from ethyl cyanoacetate and α-bromoacetophenones via the 2-amino-3-ethoxycarbonyl-5- aryl-pyrroles and 4-chloro-6-arylpyrrolopyrimidines. Aromatic substitution with benzylic amines was performed by conventional thermal substitution, and palladium catalysed coupling. The two methods resulted in similar yields, but the palladium coupling had the benefit of lower chemical consumption and reduced reaction times. Eight of the new compounds had IC50 values in the range of 2.8-9.0 nM. Four of these have a fluorine atom positioned at sites otherwise potentially susceptible to oxidative metabolism. Structural variation of the 6-aryl group indicated that the inhibitory action was only moderately sensitive to modifications in this fragment. However, the potency depended strongly on the structure of the aromatic part of the 4-amino group, and any aromatic substitution except fluorine reduced the in vitro activity. The cellular EGFR internalization response of selected compounds was evaluated using HeLa cells. Three fluorinated derivatives had a pronounced effect in inhibiting EGFR internalization.