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

Base Information

• Chemical 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
• CAS No.: 146943-43-3
• Molecular Formula: C24H29 N5 O6
• Molecular Weight: 483.524
• Mol file: 146943-43-3.mol

Synonyms:L-Glutamicacid, N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-,diethyl ester (9CI); 1H-Pyrrolo[2,3-d]pyrimidine, L-glutamic acid deriv.

Chemical Property of 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

Chemical Property:

• Melting Point: 84-86 °C
• PSA: 169.26000
• Density: 1.38
• LogP: 2.59550
• Storage Temp.: Refrigerator
• Solubility.: DMSO, Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

PemetrexedDiethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of 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

There total 41 articles about 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 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

diethyl N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethenyl]benzoyl]-L-glutamate → 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 (146943-43-3)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; for 8h; under 3800.26 Torr;

Reference yield: 94.5%

diethyl-L-glutamate hydrochloride (1118-89-4) → 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 (146943-43-3)

Guidance literature:

With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; sodium hydroxide; In ethanol; water; at 40 ℃; for 3h;

Reference yield: 85.5%

4-methyl-morpholine (109-02-4) + 2-chloro-4,6-dimethoxy-1 ,3,5-triazine (3140-73-6) + diethyl-L-glutamate hydrochloride (1118-89-4) + 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid (137281-39-1) → 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 (146943-43-3) + 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-morpholine (241483-00-1)

Guidance literature:

4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid; In N,N-dimethyl-formamide; at 20 ℃; for 1h; Cooling with ice; Inert atmosphere;

diethyl-L-glutamate hydrochloride; In N,N-dimethyl-formamide; at 35 ℃; for 2h; Inert atmosphere;

DOI:10.1002/jhet.2164

upstream raw materials:

L-glutamic acid diethyl ester

4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid

diethyl-L-glutamate hydrochloride

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

Refernces

• 1、 Qi,Wen,Li,Bai,Chen,Wang. "An Efficient Synthesis of Pemetrexed Disodium". . p. 1565 - 1569. Retrieved 2015/10/06.
• 2、 Mitchell-Ryan, Shermaine,Wang, Yiqiang,Raghavan, Sudhir,Ravindra, Manasa Punaha,Hales, Eric,Orr, Steven,Cherian, Christina,Hou, Zhanjun,Matherly, Larry H.,Gangjee, Aleem. "Discovery of 5-substituted pyrrolo[2,3- d ]pyrimidine antifolates as dual-acting inhibitors of glycinamide ribonucleotide formyltransferase and 5-aminoimidazole-4-carboxamide ribonucleotide formyltransferase in de novo purine nucleotide biosynthesis: Implications of inhibiting 5-aminoimidazole-4- carboxamide ribonucleotide formyltransferase to AMPK activation and antitumor activity". . p. 10016 - 10032. Retrieved 2014/01/17.