179928-10-0

Basic information

• Product Name: 6-bromo-3-[(4-methylphenyl)sulfonyl]pyrrolo[1,2-c]pyrimidine
• Synonyms: 6-bromo-3-[(4-methylphenyl)sulfonyl]pyrrolo[1,2-c]pyrimidine
• CAS NO: 179928-10-0
• Molecular Weight: 351.224
• Mol File: 179928-10-0.mol

Chemical Properties

• CAS DataBase Reference: 6-bromo-3-[(4-methylphenyl)sulfonyl]pyrrolo[1,2-c]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromo-3-[(4-methylphenyl)sulfonyl]pyrrolo[1,2-c]pyrimidine(179928-10-0)
• EPA Substance Registry System: 6-bromo-3-[(4-methylphenyl)sulfonyl]pyrrolo[1,2-c]pyrimidine(179928-10-0)

Safety Data

• Hazardous Substances Data: 179928-10-0(Hazardous Substances Data)

Upstream product

• 1003-29-8 2-pyrrole aldehyde 
• 931-33-9 4-bromopyrrole-2-carboxaldehyde 
• 5697-44-9 p-tolylsulfonylmethyl isocyanide 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 

Downstream Products

• 5910-05-4 methyl 2-formyl-4-pyrrolcarboxylate 
• 179928-19-9 6-methylpyrrolo[1,2-c]pyrimidine 
• 179928-11-1 6-methyl-3-[(4-methylphenyl)sulfonyl]pyrrolo[1,2-c]pyrimidine 

Relevant articles and documents

Structure-activity relationships (SAR) and structure-kinetic relationships (SKR) of sulphone-based CRTh2 antagonists

Monocyclic and bicyclic ring systems were investigated as the "core" section of a series of diphenylsulphone-containing acetic acid CRTh2 receptor antagonists. A range of potencies were observed and single-digit nanomolar potencies were obtained in both the monocyclic and bicyclic cores. Residence times for the monocyclic compounds were very short. Some of the bicyclic cores displayed better residence times. A methyl group in the northern part of the core, between the head and tail was a necessary requirement for the beginnings of long residence times. Variations of the tail substitution maximised potencies and residence times.

Pyrrolodiazines. 5. Synthesis, structure, and chemistry of pyrrolo[1,2- c]pyrimidine. Dipolar cycloaddition of pyrrolo[1,2-c]pyrimidinium ylides

An improved synthesis of pyrrolo[1,2-c]pyrimidines, including the parent system, was accomplished via sequential condensation of substituted pyrrole- 2-carboxaldehydes with tosylmethyl isocyanide (TOSMIC), followed by desulfonylation of the formed tosylpyrrolo[1,2-c]pyrimidines. Based on the ab initio calculations performed on the pyrrolo[1,2-c]pyrimidine 1a, some of the basic chemistry was investigated, including electrophilic substitution, addition of organolithium reagents, metalation with lithium diisopropylamide (LDA) and subsequent reaction with electrophiles, and formation of salts by quaternization of the nonbridgehead nitrogen. Azomethine ylides generated from pyrrolo[1,2-c]pyrimidinium salts undergo 1,3-dipolar cycloaddition with suitable dipolarophiles to give new dipyrrolo[1,2-a;1',2'-c]pyrimidine derivatives, with high regio- and stereoselectivity.

Improved synthesis of pyrrolo[1,2-c]pyrimidine and derivatives

An improved synthesis of pyrrolo[1,2-c]pyrimidine derivatives by cyclocondensation of pyrrole-2-carboxaldehydes with tosylmethyl isocyanide followed by desulfonylation of the resulting 2-tosylpyrrolo[1,2-c]- pyrimidines with sodium amalgam is described.