492439-13-1

Basic information

• Product Name: 7-acetyl-9-benzylamino-4-methoxypyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine
• Synonyms: 7-acetyl-9-benzylamino-4-methoxypyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine
• CAS NO: 492439-13-1
• Molecular Weight: 346.389
• Mol File: 492439-13-1.mol

Chemical Properties

• CAS DataBase Reference: 7-acetyl-9-benzylamino-4-methoxypyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 7-acetyl-9-benzylamino-4-methoxypyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine(492439-13-1)
• EPA Substance Registry System: 7-acetyl-9-benzylamino-4-methoxypyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine(492439-13-1)

Safety Data

• Hazardous Substances Data: 492439-13-1(Hazardous Substances Data)

Upstream product

• 917-54-4 methyllithium 
• 492439-09-5 9-benzylamino-4-methoxypyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine-7-carboxylic acid 
• 290333-02-7 4-methoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde 
• 82257-15-6 4-methoxynicotinaldehyde 
• 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 

Downstream Products

• 492439-25-5 7-(2-Amino-pyrimidin-4-yl)-9-benzylamino-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-4-ol 
• 492439-23-3 [7-(2-Amino-pyrimidin-4-yl)-4-methoxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-9-yl]-benzyl-amine 
• 878020-42-9 5,7-Bis-(2-amino-pyrimidin-4-yl)-9-benzylamino-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-4-ol 
• 878020-40-7 Benzyl-[5,7-bis-(2-amino-pyrimidin-4-yl)-4-methoxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-9-yl]-amine 

Relevant articles and documents

Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B

The marine alkaloid variolin B 2 and eight synthetic derivatives with different substituents at positions C-5 and C-7 have been tested in a panel of sixteen human tumor cell lines to evaluate their cytotoxic potential.

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.