4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER

Base Information

• Chemical Name: 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER
• CAS No.: 519032-08-7
• Molecular Formula: C17H19N3O6
• Molecular Weight: 361.354
• Hs Code.: 2933599090
• Mol file: 519032-08-7.mol

Synonyms:methyl2-[1-[[(benzyloxy)carbonyl]amino]-1-methylethyl]-5,6-dihydroxypyrimidine-4-carboxylate;1,6-Dihydro-5-hydroxy-2-[1-methyl-1-[[benzylcarbamoyl]amino]ethyl]-6-oxo-4-pyrimidinecarboxylic Acid Methyl Ester;

Chemical Property of 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER

Chemical Property:

• Appearance/Colour: Brown solid
• Vapor Pressure: 8.09E-13mmHg at 25°C
• Melting Point: 186.3-187.0 °C
• Refractive Index: 1.596
• Boiling Point: 552.6 °C at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 288 °C
• PSA: 130.61000
• Density: 1.354 g/cm³
• LogP: 1.81450
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

1,6-Dihydro-5-hydroxy-2-[1-methyl-1-[[benzylcarbamoyl]amino]ethyl]-6-oxo-4-pyrimidinecarboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate in the preparation of HIV-integrase inhibitors

Technology Process of 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER

There total 6 articles about 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, 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: 58.0%

[1-(N'-hydroxycarbamimidoyl)-1-methyl-ethyl]carbamic acid benzyl ester (518047-98-8) + dimethyl acetylenedicarboxylate (762-42-5) → methyl 2-(1-{[(benzyloxy) carbonyl] amino}-1-methylethyl)-5,6-dihydroxypyrimidine-4-carboxylate (519032-08-7)

Guidance literature:

[1-(N'-hydroxycarbamimidoyl)-1-methyl-ethyl]carbamic acid benzyl ester; dimethyl acetylenedicarboxylate; In methanol; at 20 ℃; for 2h;

With xylene; In methanol; at 90 - 120 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.09.070

Reference yield:

(cyano-dimethyl-methyl)carbamic acid benzyl ester (100134-82-5) → methyl 2-(1-{[(benzyloxy) carbonyl] amino}-1-methylethyl)-5,6-dihydroxypyrimidine-4-carboxylate (519032-08-7)

Guidance literature:

Multi-step reaction with 3 steps

1: NH₂OH / methanol / 60 °C

2: CHCl₃ / 3 h / 60 °C

3: xylene / Heating

With hydroxylamine; In methanol; chloroform; xylene;

DOI:10.1021/jm070027u

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → methyl 2-(1-{[(benzyloxy) carbonyl] amino}-1-methylethyl)-5,6-dihydroxypyrimidine-4-carboxylate (519032-08-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / Na₂CO₃ / 20 °C

2: NH₂OH / methanol / 60 °C

3: CHCl₃ / 3 h / 60 °C

4: xylene / Heating

With hydroxylamine; sodium carbonate; In methanol; chloroform; xylene;

DOI:10.1021/jm070027u

upstream raw materials:

2-[(2-benzyloxycarbonylamino-2-methyl-propionimidoyl)-aminooxy]-but-2-enedioic acid dimethyl ester

benzyl [2-amino-2-(hydroxyimino)-1,1-dimethylethyl]carbamate

(cyano-dimethyl-methyl)carbamic acid benzyl ester

benzyl chloroformate

Downstream raw materials:

methyl 5-(benzoyloxy)-2-(1-{[(benzyloxy)carbonyl]amino}-1-methylethyl)-6-hydroxypyrimidine-4-carboxylate

C₂₃H₂₄N₄O₅

C₂₃H₂₃ClN₄O₅

C₂₄H₂₆N₄O₅

Refernces

• 1、 Summa, Vincenzo,Petrocchi, Alessia,Bonelli, Fabio,Crescenzi, Benedetta,Donghi, Monica,Ferrara, Marco,Fiore, Fabrizio,Gardelli, Cristina,Paz, Odalys Gonzalez,Hazuda, Daria J.,Jones, Philip,Kinzel, Olaf,Laufer, Ralph,Monteagudo, Edith,Muraglia, Ester,Nizi, Emanuela,Orvieto, Federica,Pace, Paola,Pescatore, Giovanna,Scarpelli, Rita,Stillmock, Kara,Witmer, Marc V.,Rowley, Michael. "Discovery of raltegravir, a potent, selective orally bioavailable HIV-integrase inhibitor for the treatment of HIV-AIDS infection". experimental part. p. 5843 - 5855. Retrieved 2009/09/25.