518048-03-8

Basic information

• Product Name: 2-(1-AMINO-1-METHYLETHYL)-N-(4-FLUOROBENZYL)-5-HYDROXY-1-METHYL-6-OXO-1,6-DIHYDROPYRIMIDINE-4-CARBOXAMIDE
• Synonyms: 2-(1-AMINO-1-METHYLETHYL)-N-(4-FLUOROBENZYL)-5-HYDROXY-1-METHYL-6-OXO-1,6-DIHYDROPYRIMIDINE-4-CARBOXAMIDE;2-(2-aminopropan-2-yl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide;InterMediate B of Raltegravir;2-(2-AMinopropan-2-yl)-N-(4-fluorobenzyl)-5-hydroxy-1-ethyl-6-oxo-1,6-dihydropyriMidine-4-carboxaMide;2-(2-aMinopropan-2-yl)-N-[(4-fluorophenyl)Methyl]-5-hydroxy-1-Methyl-6-oxo-1,6-dihydropyriMidine-4-carboxaMide;2-(1-AMino-1-Methylethyl)-N-[(4-fluorophenyl)Methyl]-1,6-dihydro-5-hydroxy-1-Methyl-6-oxo-;N-(4-fluorobenzyl)-2-(2-aMinopropan-2-yl)-5-hydroxy-1-Methyl-6-oxo-1,6-dihydropyriMidine-4-carboxaMide;2-(2-Aminopropan-2-yl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carbox
• CAS NO: 518048-03-8
• Molecular Formula: C₁₆H₁₉FN₄O₃
• Molecular Weight: 334.35
• EINECS: 1592732-453-0
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Isotope Labelled Compounds;intermediate;Fluorine series
• Mol File: 518048-03-8.mol
• Article Data: 15

Chemical Properties

• Melting Point: 105-107°C
• Boiling Point: 567.4 °C at 760 mmHg
• Flash Point: 311 °C
• Appearance: White solid (powder)
• Density: 1.35
• Refractive Index: 1.607
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Very Slightly, Heated), Pyridine (Slightly)
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 2-(1-AMINO-1-METHYLETHYL)-N-(4-FLUOROBENZYL)-5-HYDROXY-1-METHYL-6-OXO-1,6-DIHYDROPYRIMIDINE-4-CARBOXAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-AMINO-1-METHYLETHYL)-N-(4-FLUOROBENZYL)-5-HYDROXY-1-METHYL-6-OXO-1,6-DIHYDROPYRIMIDINE-4-CARBOXAMIDE(518048-03-8)
• EPA Substance Registry System: 2-(1-AMINO-1-METHYLETHYL)-N-(4-FLUOROBENZYL)-5-HYDROXY-1-METHYL-6-OXO-1,6-DIHYDROPYRIMIDINE-4-CARBOXAMIDE(518048-03-8)

Safety Data

• Hazardous Substances Data: 518048-03-8(Hazardous Substances Data)

Usage

Description

2-(1-Amino-1-methylethyl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide is a complex organic compound characterized by its chemical structure and properties. It is a white solid (powder) and serves as an important intermediate in the synthesis of HIV-integrase inhibitors, which are crucial in the development of antiretroviral drugs for the treatment of HIV/AIDS.

Uses

1. Pharmaceutical Industry:
2-(1-Amino-1-methylethyl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide is used as an intermediate in the preparation of HIV-integrase inhibitors for the development of antiretroviral drugs. Its role in this process is to facilitate the creation of compounds that can effectively inhibit the integration of the HIV virus into the host's DNA, thus suppressing the viral replication process.
2. Research and Development:
In the field of research and development, this compound is used as a labeled intermediate in the preparation of labeled HIV-integrase inhibitors. This application is essential for studying the mechanism of action, pharmacokinetics, and pharmacodynamics of these inhibitors, as well as for the development of new and more effective antiretroviral therapies.
3. Chemical Synthesis:
As a white solid (powder), 2-(1-Amino-1-methylethyl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide can also be used in various chemical synthesis processes, potentially leading to the development of new compounds with diverse applications in different industries.

InChI:InChI=1/C16H19FN4O3/c1-16(2,18)15-20-11(12(22)14(24)21(15)3)13(23)19-8-9-4-6-10(17)7-5-9/h4-7,22H,8,18H2,1-3H3,(H,19,23)

Upstream product

• 140-75-0 para-fluorobenzylamine 
• 519028-33-2 benzyl 2-(4-(4-fluorobenzylcarbamoyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-ylcarbamate 
• 888504-27-6 2-(1-benzyloxycarbonylamino-1-methyl-ethyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid methyl ester 
• 518048-02-7 {1-[4-(4-fluoro-benzylcarbamoyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidin-2-yl]-1-methyl-ethyl}carbamic acid benzyl ester 

Downstream Products

• 518048-05-0 raltegravir 
• 518048-04-9 methyl {[1-(4-{[(4-fluorobenzyl)amino]carbonyl}-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)-1-methylethyl]amino}(oxo)acetate 
• 1064707-02-3 N-(4-fluorobenzyl)-5-hydroxy-1-methyl-2-(1-methyl-1-[(pyridin-2ylcarbonyl)amino]ethyl)-6-oxo-1,6-dihydropyrimidine-4-carboxamide 
• 1064707-06-7 N-(4-fluorobenzyl)-5-hydroxy-1-methyl-2-{1-methyl-1-[(1,3-thiazol-5-ylcarbonyl)amino]ethyl}-6-oxo-1,6-dihydropyrimidine-4-carboxamide 
• 1064707-04-5 N-[1-(4-{[(4-fluorobenzyl)amino]carbonyl}-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)-1-methylethyl]pyrimine-2-carboxamide 
• 1064707-07-8 N-(4-fluorobenzyl)-5-hydroxy-1-methyl-2-{1-methyl-1-{[(5-methyl-4H-1,2,4-triazol-3-yl)carbonyl]amino}ethyl}-6-oxo-1,6-dihydropyrimidine-4-carboxamide 
• 1064706-92-8 2-(1-dimethylamino-1-methylethyl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide 
• 1064706-95-1 N-(4-fluorobenzyl)-5-hydroxy-1-methyl-2-{1-methyl-1-[(methylsulfonyl)amino]ethyl}-6-oxo-1,6-dihydropyrimidine-4-carboxamide 
• 518049-93-9 N-(4-fluorobenzyl)-5-hydroxy-1-methyl-2-{1-[(1H-imidazol-5-ylcarbonyl)amino]-1-methylethyl}-6-oxo-1,6-dihydropyrimidine-4-carboxamide 
• 1064706-97-3 2-(1-{[(dimethylamino)sulfonyl]amino}-1-methylethyl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide 
• 1328839-28-6 C₂₄H₂₃FN₈O₇ 
• 1172131-68-8 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 
• 1193687-88-5 ethyl (2-(4-(4-fluorobenzylcarbamoyl)-1,6-dihydro-5-hydroxy-1-methyl-6-oxopyrimidin-2-yl)propan-2-ylcarbamoyl)formate 

Relevant articles and documents

A Facile Synthesis of Raltegravir Potassium—An HIV Integrase Inhibitor

A facile, cost-effective, and commercially viable synthesis of Raltegravir Potassium (1) has been developed from 2-(1-amino-1-methyl-ethyl)-N-[(4-fluorophenyl)methyl]-1,6-dihydro-5-hydroxy-1-methyl-6-oxo-4-pyrimidinecarboxamide (9) with high purity and in good yields. In addition, a new approach for the synthesis of key amine intermediate (9) of Raltegravir Potassium (1) from commercially available 2-amino-2-methylpropanenitrile hydrochloride (2) is also described. The key features of the synthesis are fewer synthetic steps, employing the inexpensive reagents and eco-friendly.

Preparation method of pyrimidinone amide type compound

The invention discloses a pyrimidinone amide type compound and a preparation method thereof. A pyrimidinone compound is taken as a starting material and is subjected to four-step chemical conversion to obtain TN-A005 and an analogue thereof, and an intermediate can be prepared from methyl tetrazole. A one-pot method is used for feeding in the whole preparation process, post-treatment purificationof each step is recrystallization or dispersion washing, the use of means such as silica gel column chromatography is avoided, the preparation technology is greatly simplified, the preparation efficiency is improved, and the total yield can reach 50%. The method is simple and convenient in preparation steps and can improve the preparation efficiency.

PROCESS FOR PREPARING COMPOUNDS USEFUL AS INTERMEDIATES FOR THE PREPARATION OF RALTEGRAVIR

The invention discloses a novel and selective methylation process used in the preparation of Raltegravir and intermediates. Further disclosed is an improved method for the reaction of intermediate amine compound of formula IIb with oxadiazole intermediate compound of formula V.