117663-59-9

Basic information

• Product Name: 2,4-dis(ethoxycarbonyl)-6-(N,N-dibenzylamino)-5-methylpyrimidine
• Synonyms: 2,4-dis(ethoxycarbonyl)-6-(N,N-dibenzylamino)-5-methylpyrimidine
• CAS NO: 117663-59-9
• Molecular Weight: 433.507
• Mol File: 117663-59-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,4-dis(ethoxycarbonyl)-6-(N,N-dibenzylamino)-5-methylpyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dis(ethoxycarbonyl)-6-(N,N-dibenzylamino)-5-methylpyrimidine(117663-59-9)
• EPA Substance Registry System: 2,4-dis(ethoxycarbonyl)-6-(N,N-dibenzylamino)-5-methylpyrimidine(117663-59-9)

Safety Data

• Hazardous Substances Data: 117663-59-9(Hazardous Substances Data)

Upstream product

• 898-22-6 triethyl 1,3,5-triazine-2,4,6-tricarboxylate 
• 75371-82-3 1-N,N-dibenzylamino-1-propyne 

Downstream Products

• 117663-71-5 4-(N,N-dibenzylamino)-5-methylpyrimidine 
• 142582-34-1 N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(4-amino-6-(amido-N^im-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl methyl ester)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide 
• 142582-35-2 N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(4-amino-6-(amido-N^im-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide 
• 157916-80-8 ethyl 2-<1(R)-hydroxy-2(S)-(methylthio)-2-<((4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl)carbonyl>ethyl>-6-amino-5-methylpyrimidine-4-carboxylate 
• 157968-10-0 ethyl 2-<1(S)-hydroxy-2(R)-(methylthio)-2-<((4R,5S)-4-methyl-5-phenyl-2-oxazolidinyl)carbonyl>ethyl>-6-amino-5-methylpyrimidine-4-carboxylate 
• 157916-81-9 ethyl 2-<1(S)-hydroxy-2-<((4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl)carbonyl>ethyl>-6-amino-5-methylpyrimidine-4-carboxylate 
• 157916-86-4 ethyl 2-<1(R)-hydroxy-2-<((4R,5S)-4-methyl-5-phenyl-2-oxazolidinyl)carbonyl>ethyl>-6-amino-5-methylpyrimidine-4-carboxylate 
• 147975-84-6 ethyl 2(R)-<1-<<2(S)-<((tert-butyloxy)carbonyl)amino>-2-carbamoylethyl>amino>-2-<((4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl)carbonyl>-2(S)-(methylthio)ethyl>-6-amino-5-methylpyrimidine-4-carboxylate 
• 157916-82-0 ethyl 2-<1(R)-azido-2-<((4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl)carbonyl>ethyl>-6-amino-5-methylpyrimidine-4-carboxylate 
• 147911-90-8 ethyl 2(S)-<1-<<2(S)-<((tert-butyloxy)carbonyl)amino>-2-carbamoylethyl>amino>-2-<((4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl)carbonyl>-2(S)-(methylthio)ethyl>-6-amino-5-methylpyrimidine-4-carboxylate 
• 147975-83-5 ethyl 2(R)-<1-<<2(S)-<((tert-butyloxy)carbonyl)amino>-2-carbamoylethyl>amino>-2-<((4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl)carbonyl>-2(R)-(methylthio)ethyl>-6-amino-5-methylpyrimidine-4-carboxylate 
• 147911-91-9 ethyl 2(S)-<1-<<2(S)-<((tert-butyloxy)carbonyl)amino>-2-carbamoylethyl>amino>-2-<((4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl)carbonyl>ethyl>-6-amino-5-methylpyrimidine-4-carboxylate 
• 147975-82-4 ethyl 2(R)-<1-<<2(S)-<((tert-butyloxy)carbonyl)amino>-2-carbamoylethyl>amino>-2-<((4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl)carbonyl>ethyl>-6-amino-5-methylpyrimidine-4-carboxylate 
• 142582-31-8 6-amino-4-(ethoxycarbonyl)-5-methyl-2-(((p-tolylsulfonyl)oxy)methyl)pyrimidine 

Relevant articles and documents

Total synthesis of bleomycin A2 and related agents. 2. Synthesis of (-)-pyrimidoblamic acid, epi-(+)pyrimidoblamic acid, (+)-desacetamidopyrimidoblamic acid, and (-)-descarboxamidopyrimidoblamic acid

Full details of concise syntheses of (-)-pyrimidoblamic acid (1), the authentic heterocyclic core of the bleomycin A2 metal binding domain, as well as the key substructure analogs epi-(+)-pyrimidoblamic acid (2), (+)-desacetamidopyrimidoblamic acid (3), and (-)-descarboxamidopyrimidoblamic acid (4) are described. Key to the approach is the implementation of an inverse electron demand [4+2] cycloaddition reaction of 2,4,6-tris(ethoxycarbonyl)-1,3,5-triazine with 1-(dibenzylamino)-1-propyne or in situ generated 1,1-diaminopropene for the one-step preparation of an appropriately functionalized pyrimidine nucleus. The development and subsequent implementation of a diastereoselective imine addition reaction of optically active N-acyloxazolidinone enolates provided a stereocontrolled introduction of the pyrimidoblamic acid C2 acetamido side chain. Chemical studies which unambiguously establish and confirm the absolute configuration of the C2 acetamido side chain are detailed, and their extension to the synthesis of (-)-descarboxamidopyrimidoblamic acid (4) is described.

INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF 2,4,6-TRIS(ETHOXYCARBONYL)-1,3,5-TRIAZINE AND 2,4,6-TRIS(METHYLTHIO)-1,3,5-TRIAZINE: PYRIMIDINE INTRODUCTION

A full investigation of the scope of the participation of 2,4,6-tris(ethoxycarbonyl)-1,3,5-triazine (la) and 2,4,6-tris(methylthio)-1,3,5-triazine (1b) in inverse electron demand Diels-Alder reactions suitable for the preparation of functionalized 5,6-disubstituted pyrimidines is detailed.The use of the resulting cycloadducts as immediate precursors to the parent 4,5-disubstituted pyrimidines is described.