1590459-85-0

Upstream product

• 65766-32-7 6-chloro-N-methylpyrimidin-4-amine 
• 1590459-81-6 6-chloro-5-iodo-N-methylpyrimidin-4-amine 
• 1590459-82-7 6-chloro-N-methyl-5-(2-phenylethynyl)pyrimidin-4-amine 
• 173459-05-7 4-Chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine 
• 74-88-4 methyl iodide 
• 371-40-4 4-fluoroaniline 
• 106-40-1 4-bromo-aniline 
• 106-47-8 4-chloro-aniline 
• 873-74-5 4-Aminobenzonitrile 
• 536-74-3 phenylacetylene 

Downstream Products

• 1590459-95-2 5-iodo-7-methyl-6-phenyl-4-(2-tolyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1590459-96-3 5-iodo-7-methyl-6-phenyl-4-(4-tolyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1590459-97-4 5-iodo-4-(4-methoxyphenyl)-7-methyl-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine 
• 1590459-98-5 5-iodo-7-methyl-6-phenyl-4-[4-(trifluoromethyl)phenyl]-7H-pyrrolo[2,3-d]-pyrimidine 
• 1590460-04-0 5-(4-methoxyphenyl)-7-methyl-6-phenyl-4-(3-tolyl)-7H-pyrrolo-[2,3-d]pyrimidine 
• 1590460-05-1 7-methyl-6-phenyl-4-(3-tolyl)-5-[4-(trifluoromethyl)phenyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 1590460-06-2 7-methyl-6-phenyl-4-(3-tolyl)-5-(4-tolyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1590460-07-3 7-methyl-6-phenyl-4,5-bis-(3-tolyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1590460-08-4 5-(4-methoxyphenyl)-7-methyl-6-phenyl-4-(2-tolyl)-7H-pyrrolo-[2,3-d]pyrimidine 
• 1590460-09-5 5-(4-methoxyphenyl)-7-methyl-6-phenyl-4-(4-tolyl)-7H-pyrrolo-[2,3-d]pyrimidine 
• 1590460-10-8 4,5-bis(4-methoxyphenyl)-7-methyl-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine 
• 1590460-11-9 5-(4-methoxyphenyl)-7-methyl-6-phenyl-4-[4-(trifluoromethyl)-phenyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 1590460-03-9 4-chloro-5-(4-methoxyphenyl)-7-methyl-6-phenyl-7H-pyrrolo[2,3-d]-pyrimidine 
• 1590460-01-7 5-bromo-4-chloro-7-methyl-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine 

Relevant academic research and scientific papers

Balancing potency, metabolic stability and permeability in pyrrolopyrimidine-based EGFR inhibitors

The present study describes our continuous effort to develop epidermal growth factor receptor (EGFR) inhibitors based on the 6-aryl-pyrrolo[2,3-d]pyrimidin-4-amine scaffold. The activity-ADME space has been evaluated by synthesizing 43 new structures, including four variations of the 4-amino group and 34 different substitution patterns in the 6-aryl moiety. Most of the new pyrrolopyrimidines were highly active, with twelve analogues possessing lower IC50values than the commercial drug Erlotinib in enzymatic assays. Ten EGFR inhibitors were also profiled in cell studies using the Ba/F3-EGFRL858Rreporter cells, and all revealed nanomolar activity. However, some of the privileged structures in terms of potency had ADME short-comings: compounds containing amides, sulfonamides, amine and hydroxymethyl substituents in the 6-aryl group had low permeability and high efflux, derivatives having (R)-3-amino-3-phenylpropan-1-ol at C-4 induced hERG inhibition properties, and metabolic lability was seen for compounds having (S)-2-methoxy-1-phenylethan-1-amine at C-4. Based on a trade-off between enzymatic activity, cellular potency and ADME properties, (S)-2-phenyl-2-((6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethan-1-ol appeared as the most promising drug candidate. Cellular studies indicate this compound to have therapeutic use in EGFR driven diseases.

One-pot synthesis of 4-aminated pyrrolo[2,3-d]pyrimidines from alkynylpyrimidines under metal-catalyst-free conditions

A novel, general, and efficient one-pot sequential reaction toward a variety of 4-aminated-6-arylpyrrolo[2,3-d]pyrimidines from 5-alkynylpyrimidines has been developed. Microwave-assisted metal-free intramolecular cyclization and amination provided moderate to excellent yields of 4-aminated pyrrolo[2,3-d]pyrimidines in short reaction times. This method avoids the use of metal-catalyst and expensive additives and was shown to tolerate amines and anilines.

Microwave-assisted synthesis of substituted pyrrolo[2,3-d]pyrimidines

A new synthetic route to triaryl pyrrolo[2,3-d]pyrimidines from common 4,6-dichloropyrimidine has been developed. The triarylated compounds are synthesized by three cross-coupling reactions using three different catalysts. The introduction of a C-6 aryl group was achieved in a two-step process under Sonogashira conditions [Pd(dba)2/CuI] followed by intramolecular cyclization, and application of Suzuki-Miyaura conditions [Pd(PPh 3)4; PdCl2(PPh3)2] led to C-4 and C-5 diarylation. This sequence allows a flexible synthetic approach to highly arylated pyrrolopyrimidines containing different aryl groups. A new synthetic route to triaryl pyrrolo[2,3-d]pyrimidines from common 4,6-dichloropyrimidine has been developed. The triarylated compounds are synthesized by three cross-coupling reactions using three different catalysts. Copyright

Microwave-Assisted Synthesis of Substituted Pyrrolo[2,3-d]pyrimidines

A new synthetic route to triaryl pyrrolo[2,3-d]pyrimidines from common 4,6-dichloropyrimidine has been developed. The triarylated compounds are synthesized by three cross-coupling reactions using three different catalysts. The introduction of a C-6 aryl group was achieved in a two-step process under Sonogashira conditions [Pd(dba)2/CuI] followed by intramolecular cyclization, and application of Suzuki-Miyaura conditions [Pd(PPh3)4; PdCl2(PPh3)2] led to C-4 and C-5 diarylation. This sequence allows a flexible synthetic approach to highly arylated pyrrolopyrimidines containing different aryl groups.