146943-43-3

Basic information

• Product Name: N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester
• Synonyms: (S)-Diethyl 2-(4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedioate;N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester;PeMetrexed diethyl ester (L-GlutaMic acid, N-[4-[2-(2-aMino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl]benzoyl]-, 1,5-diethyl ester );PeMetrexed Diethyl Ester
• CAS NO: 146943-43-3
• Molecular Formula: C₂₄H₂₉N₅O₆
• Molecular Weight: 483.52
• Mol File: 146943-43-3.mol
• Article Data: 15

Chemical Properties

• Melting Point: 84-86 ºC
• Appearance: /
• Density: 1.38
• Storage Temp.: Refrigerator
• Solubility: DMSO, Methanol (Slightly)
• CAS DataBase Reference: N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester(146943-43-3)
• EPA Substance Registry System: N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester(146943-43-3)

Safety Data

• Hazardous Substances Data: 146943-43-3(Hazardous Substances Data)

Usage

Uses

Pemetrexed Diethyl Ester is an protected intermediate in the synthesis of Pemetrexed (P219500), an multitargeted antifolate that inhibits thymidylate synthase as well as other folate dependent enzymes.

Upstream product

• 16450-41-2 L-glutamic acid diethyl ester 
• 137281-39-1 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid 
• 1118-89-4 diethyl-L-glutamate hydrochloride 
• 243636-78-4 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 
• 151864-81-2 ethyl 4-(3-oxopropyl)benzoate 
• 259145-25-0 4-(3-hydroxy-4-nitrobutyl)benzoic acid ethyl ester 
• 229470-22-8 4-[3-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-4-nitrobutyl]benzoic acid ethyl ester 
• 348620-55-3 2-amino-4-oxo-5-vinyl-7-(3',4'-dimethoxybenzyl)-3,4,5,6-tetrahydropyrrolo[2,3-d]pyrimidine 
• 348620-17-7 methyl N-crotyl-N-(3',4'-dimethoxybenzyl)malonylamide 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 229470-21-7 4-((E)-4-Nitro-but-3-enyl)-benzoic acid ethyl ester 
• 243636-63-7 methyl N-crotyl-N-(3',4'-dimethoxybenzyl)malonamide 
• 65874-27-3 4-(tert-butoxycarbonyl)benzaldehyde 
• 137281-39-1 C₁₅H₁₄N₄O₃ 

Relevant articles and documents

A pemetrexed disodium preparation method

The invention discloses a preparation method of pemetrexed disodium, which comprises the following steps: preparing 4-(4,4-dialkoxy-1-butenyl)benzoate 6 and 4-(3-formyl-3-halo-1-propenyl)benzoate 7, carrying out ring-closing reaction on the compound 7 and 2,4-diamido-6-hydroxypyrimidine under the action of an alkali to obtain a compound 9; carrying saponification on the compound 9, and acidifying to obtain a compound 10; carrying out condensation reaction on the compound 10 and diethyl L-glutamate to obtain a compound 11; carrying out catalytic hydrogenation reaction on the compound 11 under the action of a catalyst to obtain a compound 12; and carrying out hydrolysis reaction on the compound 12 under the action of an alkali to obtain the target product pemetrexed disodium 1. The method has the advantages of accessible raw materials, wide sources, low preparation cost and low price, is suitable for industrial production, and solves the problems of high preparation cost and difficulty for industrial production in the prior art.

PROCESS FOR THE PREPARATION OF PEMETREXED AND LYSIN SALT THEREOF

The present invention refers to a process for the synthesis of pemetrexed and salts thereof, in particular to a lysine salt thereof, to said salt as such and to pharmaceutical compositions that comprise the same. Furthermore, the present disclosure also relates to a crystalline form of the synthesis intermediate pemetrexed diethyl ether and a crystalline form of the pemetrexed lysine salt.

PROCESS FOR PREPARATION OF HIGHLY PURE DIALKYL PEMETREXED

The invention discloses a process for preparation of highly pure dialkyl pemetrexed by reacting a 2-(4-hydroxy-6-aminopyrrolo(2,3-d)pyrimidin-3-yl)ethylbenzoic acid with a glutamatic acid diester or its salt in presence of a safe, mild, inexpensive, non-oxidative and easy to handle reagent such as substituted triphenyl phosphate. The invention further discloses purification of dialkyl pemetrexed by crystallization or trituration and conversion of purified dialkyl pemetrexed to pemetrexed or its disodium salt.