126016-78-2

Upstream product

• 1118-89-4 diethyl-L-glutamate hydrochloride 
• 151723-87-4 4-<2-(2-amino-4,5,6,7-tetrahydro-4-oxo-3H-pyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoic acid 
• 243636-57-9 diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-(α-methylbenzyl)pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate 
• 243636-52-4 1-(α-methylbenzyl)-3-methoxycarbonyl-4-vinyl-2-pyrrolidinone 
• 243636-55-7 1-(α-methylbenzyl)-3-methoxycarbonyl-4-vinyl-2-pyrrolidinethione 
• 243636-56-8 2-amino-4-oxo-5-vinyl-7-(α-methylbenzyl)-3,4,5,6-tetrahydropyrrolo[2,3-d]pyrimidine 
• 348620-14-4 methyl N-crotyl-N-(α-methylbenzyl)malonylamide 
• 120363-13-5 tert-butyl 4-iodobenzoate 
• 134372-99-9 3-(4-<2,2-dimethylethyl>carboxyphenyl)-1-propanal 
• 153170-76-4 4-<2-(2-thiocarbonyl-3-carboethoxypyrrolidin-4-yl)ethyl>benzoic acid 
• 125991-44-8 methyl 4-[2-(2-amino-4-hydroxy-7H-5,6-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoate 
• 153170-75-3 4-<2-(2-thiocarbonyl-3-carboethoxypyrrolidin-4-yl)ethyl>benzoic acid 2,2-dimethylethyl ester 
• 153170-71-9 4-<2-(2-oxo-3-carboethoxypyrrolidin-4-yl)ethyl>benzoic acid, 2,2-dimethylethyl ester 
• 151723-79-4 2-ethylcarboxy-5-(4-(2,2-dimethylethyl)carboxyphenyl)-2-pentenoic acid ethyl ester 

Downstream Products

• 126016-79-3 N-[4-[2-(2-amino-4-hydroxy-5,6-dihydropyrrolo[2,3-d]-pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 

Relevant academic research and scientific papers

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.

SYNTHESIS OF LY288601, A 5,6-DIHYDROPYRROLOPYRIMIDINE BASED ANTIFOLATE COMPOUND RELATED TO LY231514

An expeditious synthesis of LY288601 (2), the 5,6-dihydro analog of the pyrrolopyrimidine-based antifolate compound LY231514 (1a), is described.The synthesis proceeds in eight steps from tert-butyl 4-iodobenzoate and involves the elaboration of a 2

Intermediates, and processes thereto, for the preparation of 5,6-dihydropyrrolo[2,3-d]pyrimidines

This invention relates to intermediates and processes thereto, for the preparation of 5,6-dihydropyrro[2,3-d]pyrimidines which are useful for the treatment of susceptible neoplasms

Pyrrolopyrimidine derivatives, their production and use

A compound of the formula STR1 wherein the ring A is a pyrrole or pyrroline ring, X is an amino group or a hydroxyl group, Y is a hydrogen atom, an amino group or a hydroxyl group, R is a hydrogen atom, a fluorine atom, an alkyl group, an alkenyl group or an alkynyl group, --COOR1 and --COOR2 are independently carboxyl groups which may be esterified and n is an integer of 2 to 4, and R may be different in each of the n repeating units, and salts thereof have excellent antitumor effects, and can be used as antitumor agents in mammals.