5-Pyrimidinecarboxylic acid, 1-(aminocarbonyl)-1,2,3,6-tetrahydro-4-methyl-6-(3-nitrophenyl)-2-oxo-, 1-methylethyl ester, (6R)-

Base Information

• Chemical Name: 5-Pyrimidinecarboxylic acid, 1-(aminocarbonyl)-1,2,3,6-tetrahydro-4-methyl-6-(3-nitrophenyl)-2-oxo-, 1-methylethyl ester, (6R)-
• CAS No.: 112795-98-9
• Molecular Formula: C16H18N4O6
• Molecular Weight: 362.342
• Mol file: 112795-98-9.mol

Synonyms:

Chemical Property of 5-Pyrimidinecarboxylic acid, 1-(aminocarbonyl)-1,2,3,6-tetrahydro-4-methyl-6-(3-nitrophenyl)-2-oxo-, 1-methylethyl ester, (6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Pyrimidinecarboxylic acid, 1-(aminocarbonyl)-1,2,3,6-tetrahydro-4-methyl-6-(3-nitrophenyl)-2-oxo-, 1-methylethyl ester, (6R)-

There total 12 articles about 5-Pyrimidinecarboxylic acid, 1-(aminocarbonyl)-1,2,3,6-tetrahydro-4-methyl-6-(3-nitrophenyl)-2-oxo-, 1-methylethyl ester, (6R)- 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: 77.3%

<1(R),6R>-1,2,3,6-tetrahydro-4-methyl-6-(3-nitrophenyl)-2-oxo-1-<<(1-phenylethyl)amino>carbonyl>-5-pyrimidinecarboxylic acid, 1-methylethyl ester (112796-00-6) → <6R>-1-(aminocarbonyl)-1,2,3,6-tetrahydro-4-methyl-6-(3-nitrophenyl)-2-oxo-5-pyrimidinecarboxylic acid, 1-methyl ester (112795-98-9)

Guidance literature:

With trifluoroacetic acid; at 75 ℃; for 4h;

DOI:10.1021/jm00106a048

Reference yield: 65.0%

Isopropyl (4R)-6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (285136-78-9) + Trichloroacetyl isocyanate (3019-71-4) → <6R>-1-(aminocarbonyl)-1,2,3,6-tetrahydro-4-methyl-6-(3-nitrophenyl)-2-oxo-5-pyrimidinecarboxylic acid, 1-methyl ester (112795-98-9)

Guidance literature:

Isopropyl (4R)-6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate; Trichloroacetyl isocyanate; In tetrahydrofuran; at 20 ℃; for 24h;

With methanol; silica gel; In tetrahydrofuran; at 20 ℃; for 48h;

DOI:10.1021/ja056092f

Reference yield:

isopropyl acetoacetate (542-08-5) → <6R>-1-(aminocarbonyl)-1,2,3,6-tetrahydro-4-methyl-6-(3-nitrophenyl)-2-oxo-5-pyrimidinecarboxylic acid, 1-methyl ester (112795-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / Yb(OTf)3; (R,R)-N,N'-(2-OH-Bn)2-N,N'-(2-Me-Py)2-1,2-Ph₂ethylenediamine / tetrahydrofuran / 20 °C

2.1: tetrahydrofuran / 24 h / 20 °C

2.2: 65 percent / silica gel; methanol / tetrahydrofuran / 48 h / 20 °C

With (+)-(R,R)-N,N'-bis(2-hydroxybenzyl)-N,N'-bis(2-pyridylmethyl)-1,2-diphenylethylenediamine; ytterbium(III) triflate; In tetrahydrofuran; 1.1: Biginelli reaction;

DOI:10.1021/ja056092f

upstream raw materials:

<1(R),6R>-1,2,3,6-tetrahydro-4-methyl-6-(3-nitrophenyl)-2-oxo-1-<<(1-phenylethyl)amino>carbonyl>-5-pyrimidinecarboxylic acid, 1-methylethyl ester

Isopropyl (4R)-6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Trichloroacetyl isocyanate

isopropyl acetoacetate