1337532-92-9

Basic information

• Product Name: 5-broMothieno[2,3-d]pyriMidin-4-aMine
• Synonyms: 5-broMothieno[2,3-d]pyriMidin-4-aMine
• CAS NO: 1337532-92-9
• Molecular Formula: C₆H₄BrN₃S
• Molecular Weight: 230.08506
• Mol File: 1337532-92-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 403.5±40.0 °C(Predicted)
• Appearance: /
• Density: 1.950±0.06 g/cm3(Predicted)
• PKA: 4.53±0.40(Predicted)
• CAS DataBase Reference: 5-broMothieno[2,3-d]pyriMidin-4-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-broMothieno[2,3-d]pyriMidin-4-aMine(1337532-92-9)
• EPA Substance Registry System: 5-broMothieno[2,3-d]pyriMidin-4-aMine(1337532-92-9)

Safety Data

• Hazardous Substances Data: 1337532-92-9(Hazardous Substances Data)

Usage

Description

5-Bromothieno[2,3-d]pyrimidin-4-amine is a chemical compound belonging to the class of thienopyrimidines. It is characterized by the presence of a bromine atom at the 5th position, a thieno ring, and an amine functional group at the 4th position. 5-broMothieno[2,3-d]pyriMidin-4-aMine exhibits unique chemical properties and reactivity, making it a valuable building block in the synthesis of various pharmaceutically relevant molecules.

Uses

Used in Pharmaceutical Industry:
5-Bromothieno[2,3-d]pyrimidin-4-amine is used as a key intermediate in the synthesis of Imidazolidinone derivatives. These derivatives have been identified as potent inhibitors of the protein kinase R (PKR)-like endoplasmic reticulum kinase (PERK), which plays a crucial role in the unfolded protein response (UPR). PERK inhibition has been shown to be beneficial in the treatment of various diseases, including neurodegenerative disorders, metabolic diseases, and certain types of cancer.
In the preparation of Imidazolidinone derivatives, 5-Bromothieno[2,3-d]pyrimidin-4-amine serves as a valuable starting material due to its unique structural features and reactivity. The bromine atom at the 5th position can be easily replaced with other functional groups, while the amine group at the 4th position can be used for further functionalization and diversification of the molecule. This allows for the development of a wide range of Imidazolidinone derivatives with varying potencies and selectivities against PERK, ultimately leading to the discovery of more effective therapeutic agents for the treatment of various diseases.

Upstream product

• 814918-95-1 5-bromo-4-chlorothieno[2,3-d]pyrimidine 
• 14080-50-3 thieno[2,3-d]pyrimidin-4(1H)-one 
• 56844-12-3 6-bromo-4-chlorothieno[2,3-d]pyrimidine 

Downstream Products

• 1571111-36-8 6-(4-aminothieno[2,3-d]pyrimidin-5-yl)-N-phenyl-1-naphthalenecarboxamide 
• 1337531-23-3 5-{1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl} thieno[2,3-d]pyrimidin-4-amine 
• 1337531-56-2 5-{1-[(3-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}thieno[2,3-d]pyrimidin-4-amine 

Relevant articles and documents

IMIDAZOLIDINONE DERIVATIVES AS INHIBITORS OF PERK

The invention is directed to substituted imidazolidinone derivatives. Specifically, the invention is directed to compounds according to Formula I (I) wherein R1, R2, R3, R4, R5, R6, R7, X, Y1, Y2 and Z are defined herein. The compounds of the invention are inhibitors of PERK and can be useful in the treatment of cancer, pre-cancerous syndromes, as Alzheimer's disease, neuropathic pain, spinal cord injury, traumatic brain injury, ischemic stroke, stroke, Parkinson disease, diabetes, metabolic syndrome, metabolic disorders, Huntington's disease, Creutzfeldt-Jakob Disease, fatal familial insomnia, Gerstmann-Str?ussler-Scheinker syndrome, and related prion diseases, amyotrophic lateral sclerosis, progressive supranuclear palsy, myocardial infarction, cardiovascular disease, inflammation, organ fibrosis, chronic and acute diseases of the liver, fatty liver disease, liver steatosis, liver fibrosis, chronic and acute diseases of the lung, lung fibrosis, chronic and acute diseases of the kidney, kidney fibrosis, chronic traumatic encephalopathy (CTE), neurodegeneration, dementias, frontotemporal dementias, tauopathies, Pick's disease, Neimann-Pick's disease, amyloidosis, cognitive impairment, atherosclerosis, ocular diseases, arrhythmias, in organ transplantation and in the transportation of organs for transplantation. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PERK activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

CHEMICAL COMPOUNDS ACTING AS PERK INHIBITORS

The invention is directed to substituted pyrrolidinone derivatives. Specifically, the invention is directed to compounds according to Formula X: wherein R41, R42, R43, R44, R45, R46, and R47 are defined herein. The compounds of the invention are inhibitors of PERK and can be useful in the treatment of cancer and diseases associated with activated unfolded protein response pathways, such as Alzheimer's disease, stroke, diabetes, Parkinson disease, Huntington's disease, Creutzfeldt- Jakob Disease, and related prion diseases, amyotrophic lateral sclerosis, myocardial infarction, neurodegeneration, cardiovascular disease, atherosclerosis, ocular diseases, and arrhythmias, more specifically cancers of the breast, colon, pancreas and lung. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PERK activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Discovery of 7-methyl-5-(1-{[3-(trifluoromethyl)phenyl]acetyl}-2,3-dihydro- 1H-indol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (GSK2606414), a potent and selective first-in-class inhibitor of protein kinase R (PKR)-like endoplasmic reticulum kinase (PERK)

Protein kinase R (PKR)-like endoplasmic reticulum kinase (PERK) is activated in response to a variety of endoplasmic reticulum stresses implicated in numerous disease states. Evidence that PERK is implicated in tumori-genesis and cancer cell survival stim