136784-14-0

Basic information

• Product Name: diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-benzylpyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate
• Synonyms: diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-benzylpyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate
• CAS NO: 136784-14-0
• Molecular Weight: 573.649
• Mol File: 136784-14-0.mol

Chemical Properties

• CAS DataBase Reference: diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-benzylpyrrolo[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-benzylpyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate(136784-14-0)
• EPA Substance Registry System: diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-benzylpyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate(136784-14-0)

Safety Data

• Hazardous Substances Data: 136784-14-0(Hazardous Substances Data)

Upstream product

• 116387-21-4 4-iodobenzoyl-L-glutamic acid diethyl ester 
• 348620-51-9 2-amino-4-oxo-5-vinyl-7-benzyl-3,4,5,6-tetrahydropyrrolo[2,3-d]pyrimidine 
• 100-46-9 benzylamine 
• 348620-02-0 methyl N-benzyl-N-(2-buten-1-yl)carbamate 
• 348620-15-5 methyl N-crotyl-N-benzylmalonylamide 
• 107733-62-0 benzyl crotyl amine 
• 243636-59-1 N-benzyl-N-but-2-enyl-malonamic acid methyl ester 
• 171920-15-3 Benzyl-((E)-but-2-enyl)-carbamic acid methyl ester 
• 348620-33-7 1-benzyl-3-(methoxycarbonyl)-4-vinylpyrrolidin-2-one 
• 4393-07-1 N-crotylbenzylcarbamate 
• 5817-70-9 methyl N-benzylcarbamate 

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.

A novel synthetic route to 7-substituted derivatives of the antitumor agent LY231514 (MTA)

This paper describes a further synthesis of the pyrrolo[2,3- d]pyrimidine antitumor agent MTA (LY231514). Manganic triacetate dihydrate- induced radical cyclization of methyl N-crotyl-N-(3',4'- dimethoxybenzyl)malonamide (4d) yielded the 3-carbomethoxy-2-pyrrolidinone 5d that was then thiated with P2S5 to the corresponding thiolactam (6d). Cyclization with guanidine gave the 7-substituted 2-amino-4(3H)-oxo-5,6- dihydro-pyrrolo[2,3-d]pyrimidine (7d). Pd-catalyzed coupling with diethyl 4- iodobenzoylglutamate yielded (in a single step) the diethyl ester 9d. Deprotection with H2SO4/TFA followed by saponification then gave MTA. Several additional 7-substituted derivatives of MTA were prepared by use of this methodology. In contradiction to a published claim, these 7-substituted derivatives proved to be devoid of any significant cell growth inhibitory activity.