2-(1-Amino-1-methylethyl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

Base Information

• Chemical Name: 2-(1-Amino-1-methylethyl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide
• CAS No.: 518048-03-8
• Molecular Formula: C16H19FN4O3
• Molecular Weight: 334.35
• Hs Code.: 2933599090
• Mol file: 518048-03-8.mol

Synonyms:2-(1-Amino-1-methylethyl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide;(1-Hydroxy-3-isohexenyl)naphthazarine;

Chemical Property of 2-(1-Amino-1-methylethyl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

Chemical Property:

• Appearance/Colour: White solid (powder)
• Melting Point: 105-107°C
• Refractive Index: 1.607
• Boiling Point: 567.4 °C at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 311 °C
• PSA: 110.24000
• Density: 1.373 g/cm³
• LogP: 1.84000
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Very Slightly, Heated), Pyridine (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

2-(1-Amino-1-methylethyl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-(1-Amino-1-methylethyl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

There total 9 articles about 2-(1-Amino-1-methylethyl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide 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: 100.0%

{1-[4-(4-fluoro-benzylcarbamoyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidin-2-yl]-1-methyl-ethyl}carbamic acid benzyl ester (518048-02-7) → 2-(1-amino-1-methyl-ethyl)-N-[(4-fluorophenyl)methyl]-1,6-dihydro-5-hydroxy-1-methyl-6-oxo-4-pyrimidinecarboxamide (518048-03-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol;

DOI:10.1021/jm800245z

Reference yield: 85.0%

N-[(4-fluorophenyl)methyl]-1,6-dihydro-5-hydroxy-1-methyl-2-[1-methyl-1-[[(methoxy)carbonyl]amino]ethyl]-6-oxo-4-pyrimidine carboxamide → 2-(1-amino-1-methyl-ethyl)-N-[(4-fluorophenyl)methyl]-1,6-dihydro-5-hydroxy-1-methyl-6-oxo-4-pyrimidinecarboxamide (518048-03-8)

Guidance literature:

With sodium hydroxide; In butan-1-ol; at 105 - 110 ℃; for 3h; Concentration; Solvent; Temperature; Time;

DOI:10.1002/jhet.3663

Reference yield:

C10H15N3O4 + para-fluorobenzylamine (140-75-0) → 2-(1-amino-1-methyl-ethyl)-N-[(4-fluorophenyl)methyl]-1,6-dihydro-5-hydroxy-1-methyl-6-oxo-4-pyrimidinecarboxamide (518048-03-8)

Guidance literature:

In methanol; at 65 ℃; for 3h;

upstream raw materials:

{1-[4-(4-fluoro-benzylcarbamoyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidin-2-yl]-1-methyl-ethyl}carbamic acid benzyl ester

2-(1-benzyloxycarbonylamino-1-methyl-ethyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid methyl ester

para-fluorobenzylamine

benzyl 2-(4-(4-fluorobenzylcarbamoyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-ylcarbamate

Downstream raw materials:

raltegravir

C₂₄H₂₃FN₈O₇

4-((4-fluorobenzyl)carbamoyl)-1-methyl-2-(2-((5-methyl-1,3,4-oxadiazol-2-yl)carboxamido)propan-2-yl)-6-oxo-1,6-dihydropyrimidin-5-yl benzoate

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

Refernces

• 1、 Rao, S. Venkat,Potluri, Vamsi Krishna,Potluri, Ramesh Babu. "A newfangled synthesis of integrase inhibitor drug substance raltegravir potassium". . p. 2618 - 2622. Retrieved 2019/10/02.
• 2、 Stathakis, Christos I.,Gkizis, Petros L.,Alexandraki, Elli S.,Trakossas, Sakellarios,Terzidis, Michael,Neokosmidis, Efstratios,Zacharis, Constantinos K.,Vasiliadou, Christina,Vastardi, Elli,Andreou, Thanos,Zitrou, Asteria,Varvogli, Anastasia-Aikaterini,Koftis, Theocharis V.. "(Chloromethyl)dimethylchlorosilane-KF: A Two-Step Solution to the Selectivity Problem in the Methylation of a Pyrimidone Intermediate en Route to Raltegravir". . p. 1413 - 1418. Retrieved 2017/09/22.