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

Base Information

• Chemical Name: 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-1-METHYL-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER
• CAS No.: 888504-27-6
• Molecular Formula: C₁₈H₂₁N₃O₆
• Molecular Weight: 375.381
• Hs Code.: 2933599090
• Mol file: 888504-27-6.mol

Synonyms:1,6-Dihydro-5-hydroxy-1-methyl-2-[1-methyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]-6-oxo-4-pyrimidinecarboxylic acid methyl ester

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

Chemical Property:

• Appearance/Colour: off-white solid
• Melting Point: 190-195 °C
• Refractive Index: 1.58
• PKA: 4.50±1.00(Predicted)
• PSA: 119.75000
• Density: 1.29 g/cm³
• LogP: 1.82490
• Storage Temp.: Refrigerator
• Solubility.: DMSO

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,6-Dihydro-5-hydroxy-1-methyl-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-1-METHYL-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER

There total 14 articles about 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-1-METHYL-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: 78.0%

methyl 2-(2(((benzyloxy)carbonyl)amino)propan-2-yl)-5,6-dihydroxy-1,6-dihydropyrimidine-4-carboxylate + Chloro(chloromethyl)dimethylsilane (1719-57-9) → 2-(1-benzyloxycarbonylamino-1-methyl-ethyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid methyl ester (888504-27-6)

Guidance literature:

methyl 2-(2(((benzyloxy)carbonyl)amino)propan-2-yl)-5,6-dihydroxy-1,6-dihydropyrimidine-4-carboxylate; With 1,1,1,3,3,3-hexamethyl-disilazane; In acetonitrile; at 80 ℃; for 1h; Inert atmosphere;

Chloro(chloromethyl)dimethylsilane; In acetonitrile; at 80 ℃; for 2h; Inert atmosphere;

With potassium fluoride; In ethyl acetate; at 60 ℃; for 1h; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1021/acs.oprd.7b00171

Reference yield: 70.0%

methyl 2-(2(((benzyloxy)carbonyl)amino)propan-2-yl)-5,6-dihydroxy-1,6-dihydropyrimidine-4-carboxylate + methyl iodide (74-88-4) → 2-(1-benzyloxycarbonylamino-1-methyl-ethyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid methyl ester (888504-27-6)

Guidance literature:

methyl 2-(2(((benzyloxy)carbonyl)amino)propan-2-yl)-5,6-dihydroxy-1,6-dihydropyrimidine-4-carboxylate; With magnesium methanolate; In methanol; dimethyl sulfoxide; at 40 ℃; for 0.5h; under 30 Torr;

methyl iodide; In dimethyl sulfoxide; at 20 - 60 ℃; for 7h;

With hydrogenchloride; In methanol; water; dimethyl sulfoxide; at 20 ℃; for 1h;

Reference yield: 70.0%

methyl iodide (74-88-4) → 2-(1-benzyloxycarbonylamino-1-methyl-ethyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid methyl ester (888504-27-6)

Guidance literature:

methyl 2-(2(((benzyloxy)carbonyl)amino)propan-2-yl)-5,6-dihydroxy-1,6-dihydropyrimidine-4-carboxylate; With methanol; magnesium methanolate; In dimethyl sulfoxide; at 20 - 40 ℃; for 0.666667h;

methyl iodide; In methanol; dimethyl sulfoxide; at 20 - 60 ℃; for 7h;

upstream raw materials:

methyl iodide

[1-(N'-hydroxycarbamimidoyl)-1-methyl-ethyl]carbamic acid benzyl ester

C₁₈H₂₃N₃O₇

C₁₈H₂₃N₃O₇

Downstream raw materials:

C₂₀H₂₃FN₆O₆

raltegravir

ethyl (2-(4-(4-fluorobenzylcarbamoyl)-1,6-dihydro-5-hydroxy-1-methyl-6-oxopyrimidin-2-yl)propan-2-ylcarbamoyl)formate

Refernces

• 1、 -. "PROCESS FOR PREPARING COMPOUNDS USEFUL AS INTERMEDIATES FOR THE PREPARATION OF RALTEGRAVIR". Page/Page column 22. . Retrieved 2018/04/11.
• 2、 Patil, Gulabrao D.,Kshirsagar, Siddheshwar W.,Shinde, Shivnath B.,Patil, Pankaj S.,Deshpande, Mangesh S.,Chaudhari, Ashok T.,Sonawane, Swapnil P.,Maikap, Golak C.,Gurjar, Mukund K.. "Identification, synthesis, and strategy for minimization of potential impurities observed in raltegravir potassium drug substance". . p. 1422 - 1429. Retrieved 2012/10/29.