492439-03-9

Basic information

• Product Name: 5-(2-Amino-pyrimidin-4-yl)-9-benzylamino-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-4-ol
• Synonyms: 5-(2-Amino-pyrimidin-4-yl)-9-benzylamino-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-4-ol
• CAS NO: 492439-03-9
• Molecular Weight: 383.412
• Mol File: 492439-03-9.mol

Chemical Properties

• CAS DataBase Reference: 5-(2-Amino-pyrimidin-4-yl)-9-benzylamino-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-Amino-pyrimidin-4-yl)-9-benzylamino-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-4-ol(492439-03-9)
• EPA Substance Registry System: 5-(2-Amino-pyrimidin-4-yl)-9-benzylamino-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-4-ol(492439-03-9)

Safety Data

• Hazardous Substances Data: 492439-03-9(Hazardous Substances Data)

Upstream product

• 290333-02-7 4-methoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde 
• 82257-15-6 4-methoxynicotinaldehyde 
• 492438-83-2 5-acetyl-9-benzylamino-7-ethoxycarbonyl-4-methoxypyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine 
• 492438-80-9 5-acetyl-9-benzylamino-4-methoxy-6,7-dihydropyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine 
• 492438-82-1 5-acetyl-9-benzylamino-4-methoxypyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine 
• 492438-78-5 9-benzylamino-5-bromo-4-methoxy-6,7-dihydropyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine 
• 492438-75-2 1-benzyl-3-[2-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-urea 
• 903130-44-9 2-(2-aminoethyl)-4-methoxy-7-azaindole 
• 290333-04-9 C₃₇H₄₂N₃O₄PSi 
• 290333-05-0 C₃₁H₂₈N₃O₃P 
• 290332-98-8 N-(2-trimethylsilyl)ethoxymethyl-2-ethoxycarbonyl-4-methoxypyrrolo[2,3-b]pyridine 
• 290333-00-5 [4-methoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-methanol 
• 290332-96-6 ethyl α-azido-β-(4-methoxypyrid-3-yl)acrylate 
• 290332-97-7 2-ethoxycarbonyl-4-methoxypyrrolo[2,3-b]pyridine 

Relevant articles and documents

Carbodiimide-mediated preparation of the tricyclic pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine ring system and its application to the synthesis of the potent antitumoral marine alkaloid variolin B and analog

A total synthesis of the marine alkaloid variolin B has been completed in 13 steps in an overall yield of 6.5% from 3-formyl-4-methoxypyridine. Our approach is based on the sequential formation of the 7-azaindole ring, the tricyclic pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine ring system, and finally installation of the 2-aminopyrimidine ring at C5. The required 7-azaindole ring appropriately substituted is formed by a modified indole synthesis involving a nitrene insertion process (two steps). Formation of the annelated pyrimidine ring is achieved by two routes both involving a carbodiimide-mediated cyclization process, which allow incorporation of the amine functionality at C9 of the core tricyclic (six steps). Installation of the northeast 2-aminopyrimidine ring at C5 is performed using the Bredereck protocol (three steps). Ultimate, thermal decarboxylation with concomitant O-methyl deprotection and further N-benzyl deprotection by the action of triflic acid completed the synthesis of the target natural product variolin B.