4-(8-(2,6-difluorophenyl)-2-{[2-(dimethylamino)ethyl]amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)benzoic acid

Base Information

• Chemical Name: 4-(8-(2,6-difluorophenyl)-2-{[2-(dimethylamino)ethyl]amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)benzoic acid
• CAS No.: 911370-68-8
• Molecular Formula: C₂₃H₂₂F₂N₆O₃
• Molecular Weight: 468.463
• Mol file: 911370-68-8.mol

Synonyms:4-(8-(2,6-difluorophenyl)-2-{[2-(dimethylamino)ethyl]amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)benzoic acid

Chemical Property of 4-(8-(2,6-difluorophenyl)-2-{[2-(dimethylamino)ethyl]amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(8-(2,6-difluorophenyl)-2-{[2-(dimethylamino)ethyl]amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)benzoic acid

There total 9 articles about 4-(8-(2,6-difluorophenyl)-2-{[2-(dimethylamino)ethyl]amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)benzoic 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: 77.0%

5-chloro-1-(2,6-difluorophenyl)-7-{[2-(dimethylamino)ethyl]amino}-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (911370-66-6) + 4-carboxyphenylboronic acid pinacol ester (180516-87-4) → 4-(8-(2,6-difluorophenyl)-2-{[2-(dimethylamino)ethyl]amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)benzoic acid (911370-68-8)

Guidance literature:

5-chloro-1-(2,6-difluorophenyl)-7-{[2-(dimethylamino)ethyl]amino}-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one; 4-carboxyphenylboronic acid pinacol ester; With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; at 150 ℃; for 0.583333h; Microwave irradiation;

With trifluoroacetic acid; In water; acetonitrile;

Reference yield:

4-Chloro-6-(2,6-difluoro-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbonitrile (357935-93-4) → 4-(8-(2,6-difluorophenyl)-2-{[2-(dimethylamino)ethyl]amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)benzoic acid (911370-68-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: borane-THF / tetrahydrofuran / 4 h / Heating / reflux

1.2: 0.5 h / 20 °C

1.3: pH 9.0 - 10.0

2.1: dichloromethane / 3 h / 20 °C

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.17 h / 20 °C

4.1: triethylamine / dichloromethane / 20 °C

5.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 0.58 h / 150 °C / Microwave irradiation

With borane-THF; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 5.1: Suzuki Coupling;

Reference yield:

5-(aminomethyl)-6-chloro-N-(2,6-difluorophenyl)-2-(methylthio)-4-pyrimidinamine (911370-60-0) → 4-(8-(2,6-difluorophenyl)-2-{[2-(dimethylamino)ethyl]amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)benzoic acid (911370-68-8)

Guidance literature:

Multi-step reaction with 4 steps

1: dichloromethane / 3 h / 20 °C

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.17 h / 20 °C

3: triethylamine / dichloromethane / 20 °C

4: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 0.58 h / 150 °C / Microwave irradiation

With potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; dichloromethane; water; 4: Suzuki Coupling;

upstream raw materials:

5-chloro-1-(2,6-difluorophenyl)-7-{[2-(dimethylamino)ethyl]amino}-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

4-carboxyphenylboronic acid pinacol ester

5-chloro-1-(2,6-difluorophenyl)-7-(methylsulfinyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

4-Chloro-6-(2,6-difluoro-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbonitrile