N-[4-[2-(2-AMino-4,5,6,7-tetrahydro-4,6-dioxo-1H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl]benzoyl]-L-glutaMic Acid

Base Information

• Chemical Name: N-[4-[2-(2-AMino-4,5,6,7-tetrahydro-4,6-dioxo-1H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl]benzoyl]-L-glutaMic Acid
• CAS No.: 193281-00-4
• Molecular Formula: C20H21N5O7
• Molecular Weight: 443.416
• Mol file: 193281-00-4.mol

Synonyms:N-[4-[2-(2-Amino-4,5,6,7-tetrahydro-4,6-dioxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic Acid;2-{4-[2-(2-amino-4,6-dioxo-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-pentanedioic acid;

Chemical Property of N-[4-[2-(2-AMino-4,5,6,7-tetrahydro-4,6-dioxo-1H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl]benzoyl]-L-glutaMic Acid

Chemical Property:

• Melting Point: >185°C (dec.)
• PKA: 3.59±0.10(Predicted)
• PSA: 209.05000
• Density: 1.67±0.1 g/cm3(Predicted)
• LogP: 0.88680
• Storage Temp.: Hygroscopic, Refrigerator, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)

Purity/Quality:

NLT 98% ^*data from raw suppliers

LY 338979 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: LY 338979 is a metabolite of the antifolate Pemetrexed (P219500).

Technology Process of N-[4-[2-(2-AMino-4,5,6,7-tetrahydro-4,6-dioxo-1H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl]benzoyl]-L-glutaMic Acid

There total 7 articles about N-[4-[2-(2-AMino-4,5,6,7-tetrahydro-4,6-dioxo-1H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl]benzoyl]-L-glutaMic Acid 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: 89.0%

N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-D-glutamic acid (182009-04-7) → 2-{4-[2-(2-amino-4,6-dioxo-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-pentanedioic acid (193281-00-4)

Guidance literature:

With Cumene hydroperoxide; C₃₉H₃₈AuN₆⁽¹⁺⁾*Cl^(1-); In water; 1,2-dichloro-ethane; at 50 ℃; for 3.5h; Reagent/catalyst; Solvent; Temperature;

Reference yield:

C12H12Br2O3 (1320346-37-9) → 2-{4-[2-(2-amino-4,6-dioxo-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-pentanedioic acid (193281-00-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: water; acetonitrile / 0.08 h

1.2: Reflux

2.1: sodium hydroxide / 2 h / 0 - 10 °C

3.1: 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine / N,N-dimethyl-formamide / 4 h / Reflux

4.1: sodium hydroxide / ethanol / 1 h / Cooling

With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; sodium hydroxide; In ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tetlet.2011.05.141

Reference yield:

4-methoxycarbonylphenyl bromide (619-42-1) → 2-{4-[2-(2-amino-4,6-dioxo-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-pentanedioic acid (193281-00-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: copper(l) iodide; diethylamine; triphenylphosphine; palladium dichloride / 4 h / 50 °C

1.2: 3.5 h / 2585.81 Torr

1.3: 1 h / -10 - 0 °C

2.1: hydrogen bromide; bromine; acetic acid / dichloromethane / Reflux

3.1: water; acetonitrile / 0.08 h

3.2: Reflux

4.1: sodium hydroxide / 2 h / 0 - 10 °C

5.1: 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine / N,N-dimethyl-formamide / 4 h / Reflux

6.1: sodium hydroxide / ethanol / 1 h / Cooling

With 4-methyl-morpholine; copper(l) iodide; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; hydrogen bromide; bromine; acetic acid; diethylamine; triphenylphosphine; sodium hydroxide; palladium dichloride; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tetlet.2011.05.141

upstream raw materials:

C₁₂H₁₂Br₂O₃

methyl 4-[2-(2-amino-4,6-dioxo-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoate

4-[2-(2-amino-4,6-dioxo-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoic acid

dimethyl 2-{4-[2-(2-amino-4,6-dioxo-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-pentanedioate

Refernces

• 1、 Sekhar,Acharyulu, Palle V.R.,Anjaneyulu, Yerramilli. "A short and efficient synthetic protocol for the synthesis of 5-substituted-4,6-dioxo-pyrrolo[2,3-d]pyrimidines". . p. 4140 - 4144. Retrieved 2011/09/19.