4-[2-(2-AMino-4,5,6,7-tetrahydro-4,6-dioxo-3H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl]benzoic Acid Methyl Ester

Base Information

• Chemical Name: 4-[2-(2-AMino-4,5,6,7-tetrahydro-4,6-dioxo-3H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl]benzoic Acid Methyl Ester
• CAS No.: 1320346-43-7
• Molecular Formula: C₁₆H₁₆N₄O₄
• Molecular Weight: 328.327
• Mol file: 1320346-43-7.mol

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

Chemical Property of 4-[2-(2-AMino-4,5,6,7-tetrahydro-4,6-dioxo-3H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl]benzoic Acid Methyl Ester

Chemical Property:

• Melting Point: >267°C (dec.)
• Storage Temp.: Refrigerator
• Solubility.: DMSO, Methanol

Purity/Quality:

4-[2-(2-Amino-4,5,6,7-tetrahydro-4,6-dioxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Used in the preparation of a Pemetrexed (P219500) metabolite.

Technology Process of 4-[2-(2-AMino-4,5,6,7-tetrahydro-4,6-dioxo-3H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl]benzoic Acid Methyl Ester

There total 3 articles about 4-[2-(2-AMino-4,5,6,7-tetrahydro-4,6-dioxo-3H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl]benzoic Acid Methyl 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: 85.0%

C12H12Br2O3 (1320346-37-9) + 2,6-diaminopyrimidin-4-ol (56-06-4) → methyl 4-[2-(2-amino-4,6-dioxo-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoate (1320346-43-7)

Guidance literature:

C₁₂H₁₂Br₂O₃; 2,6-diaminopyrimidin-4-ol; In water; acetonitrile; for 0.0833333h;

With sodium acetate; In water; acetonitrile; Reflux;

DOI:10.1016/j.tetlet.2011.05.141

Reference yield:

4-methoxycarbonylphenyl bromide (619-42-1) → methyl 4-[2-(2-amino-4,6-dioxo-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoate (1320346-43-7)

Guidance literature:

Multi-step reaction with 3 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

With copper(l) iodide; hydrogen bromide; bromine; acetic acid; diethylamine; triphenylphosphine; palladium dichloride; In dichloromethane; water; acetonitrile;

DOI:10.1016/j.tetlet.2011.05.141

Reference yield:

4-(4-carbomethoxyphenyl)butanal (106200-41-3) → methyl 4-[2-(2-amino-4,6-dioxo-4,5,6,7-tetrahydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoate (1320346-43-7)

Guidance literature:

Multi-step reaction with 2 steps

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

2.1: water; acetonitrile / 0.08 h

2.2: Reflux

With hydrogen bromide; bromine; acetic acid; In dichloromethane; water; acetonitrile;

DOI:10.1016/j.tetlet.2011.05.141

upstream raw materials:

C₁₂H₁₂Br₂O₃

2,6-diaminopyrimidin-4-ol

4-methoxycarbonylphenyl bromide

4-(4-carbomethoxyphenyl)butanal

Downstream raw materials:

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

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

Refernces