243636-78-4

Basic information

• Product Name: diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-(3',4'-dimethoxybenzyl)pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate
• Synonyms: diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-(3',4'-dimethoxybenzyl)pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate
• CAS NO: 243636-78-4
• Molecular Weight: 633.701
• Mol File: 243636-78-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-(3',4'-dimethoxybenzyl)pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-(3',4'-dimethoxybenzyl)pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate(243636-78-4)
• EPA Substance Registry System: diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-(3',4'-dimethoxybenzyl)pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate(243636-78-4)

Safety Data

• Hazardous Substances Data: 243636-78-4(Hazardous Substances Data)

Upstream product

• 348620-17-7 methyl N-crotyl-N-(3',4'-dimethoxybenzyl)malonylamide 
• 348620-04-2 methyl N-crotyl-N-(3',4'-dimethoxybenzyl)carbamate 
• 348620-11-1 N-crotyl-(3',4'-dimethoxybenzyl)amine 
• 243636-67-1 methyl N-(3',4'-dimethoxybenzyl)carbamate 
• 5763-61-1 3,4-dimethoxybenzylamine 
• 348620-55-3 2-amino-4-oxo-5-vinyl-7-(3',4'-dimethoxybenzyl)-3,4,5,6-tetrahydropyrrolo[2,3-d]pyrimidine 
• 116387-21-4 4-iodobenzoyl-L-glutamic acid diethyl ester 
• 243636-63-7 methyl N-crotyl-N-(3',4'-dimethoxybenzyl)malonamide 
• 243637-19-6 ((E)-But-2-enyl)-(3,4-dimethoxy-benzyl)-carbamic acid methyl ester 
• 243636-73-9 ((E)-But-2-enyl)-(3,4-dimethoxy-benzyl)-amine 

Downstream Products

• 146943-43-3 N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid diethyl ester 

Relevant articles and documents

A new route to 7-substituted derivatives of N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl) -ethyl]benzoyl}-L-glutamic acid [ALIMTA (LY231514, MTA)]

Alkylation of various primary amines with crotyl bromide, followed by DMAP-promoted acylation with methyl malonyl chloride to 4 and then manganic triacetate dihydrate/cupric acetate induced radical cyclization, gave 1-substituted-4-vinyl-3-carbomethoxy-2-pyrrolidinones (5). Thiation to the thiolactams 6 and guanidine cyclization then gave a series of 2-amino-3,4-dihydro-4-oxo-5-vinyl-7-substituted pyrrolo[2,3-d]pyrimidines (7). Palladium-catalyzed C-C coupling with diethyl 4-iodobenzoylglutamate led in one step via an unexpected redox reaction to the diethyl esters 9 of a series of 7-substituted derivatives of ALIMTA (LY231514, MTA), from which the target analogues 10 were readily prepared by saponification. Attempted deprotection at position 7 was successful in only one case (9d, R = CH2C6H3(OMe)2 (-3′,4′), which resulted in a known pentultimate precursor (9, R = H) of ALIMTA. The 7-substituted derivatives 10 proved to be inactive in vitro as inhibitors of cell division.