1,5(6H)-Pyrimidinedicarboxylic acid, 2-amino-4-methyl-6-(3-nitrophenyl)-, diethyl ester

Base Information

• Chemical Name: 1,5(6H)-Pyrimidinedicarboxylic acid, 2-amino-4-methyl-6-(3-nitrophenyl)-, diethyl ester
• CAS No.: 111199-70-3
• Molecular Formula: C17H20N4O6
• Molecular Weight: 376.369
• Mol file: 111199-70-3.mol

Synonyms:

Chemical Property of 1,5(6H)-Pyrimidinedicarboxylic acid, 2-amino-4-methyl-6-(3-nitrophenyl)-, diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,5(6H)-Pyrimidinedicarboxylic acid, 2-amino-4-methyl-6-(3-nitrophenyl)-, diethyl ester

There total 3 articles about 1,5(6H)-Pyrimidinedicarboxylic acid, 2-amino-4-methyl-6-(3-nitrophenyl)-, 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: 54.0%

2-methoxy-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, diethyl ester (111199-77-0) → 2-amino-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid bis(ethyl ester) (111199-70-3)

Guidance literature:

With ammonium acetate; ammonia; In tetrahydrofuran; for 72h; Ambient temperature;

DOI:10.1021/jo00286a020

Reference yield:

ethyl (Z)-2-(3-nitrobenzylidene)-3-oxobutanoate (39562-16-8) → 2-amino-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid bis(ethyl ester) (111199-70-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / sodium bicarbonate / dimethylformamide / 24 h / 70 °C

2: pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 54 percent / ammonium acetate, NH₃ / tetrahydrofuran / 72 h / Ambient temperature

With pyridine; ammonium acetate; ammonia; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00286a020

Reference yield:

1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid ethyl ester (106720-60-9) → 2-amino-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid bis(ethyl ester) (111199-70-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 54 percent / ammonium acetate, NH₃ / tetrahydrofuran / 72 h / Ambient temperature

With pyridine; ammonium acetate; ammonia; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00286a020

upstream raw materials:

2-methoxy-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, diethyl ester

ethyl (Z)-2-(3-nitrobenzylidene)-3-oxobutanoate

1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid ethyl ester

Downstream raw materials:

3,6-dihydro-4-methyl-2-[(methylsulfonyl)imino]-6-(3-nitrophenyl)-1,5(2H)-pyrimidinedicarboxylic acid, diethyl ester

3,4-dihydro-4-methyl-2-<(methylsulfonyl)imino>-6-(3-nitrophenyl)-1,5(2H)-pyrimidinedicarboxylic acid bis(ethyl ester)

2-(acetylamino)-3,6-dihydro-4-methyl-6-(3-nitrophenyl)-1,5(2H)-pyrimidinedicarboxylic acid bis(ethyl ester)

Refernces

• 1、 Atwal,Rovnyak,O'Reilly,Schwartz. "Substituted 1,4-dihydropyrimidines. 3.1 Synthesis of selectively functionalized 2-hetero-1,4-dihydropyrimidines". . p. 5898 - 5907. Retrieved 2007/10/02.