519032-08-7

Basic information

• Product Name: 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER
• Synonyms: InterMediate E of Raltegravir;2-(2-(BenzyloxycarbonylaMino)propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyriMidine-4-Methyl forMate;Methyl 2-[1-[[(benzyloxy)carbonyl]aMino]-1-Methylethyl]-5,6-dihydroxypyriMidine-4-carboxylate;Methyl2-(1-{[(benzyloxy)carbonyl]aMino}-1-Methylethyl)-5,6-dihydroxypyriMidine-4-carboxyllate;Methyl 2-(2-(benzyloxycarbonyl)propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyriMidine-4-carboxylate;Methyl-2-(2-{[(benzyloxy)carbo;Methyl 2-(2-(benzyloxycarbonylamino)propan-2-yl)-5-hydroxy-6-oxo-l,6-dihydropyrimidine-4-carboxylate(Raltegravir);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: 361.35
• EINECS: 1592732-453-0
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Heterocycle-Pyrimidine series
• Mol File: 519032-08-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 186.3-187.0 °C
• Boiling Point: 552.6 °C at 760 mmHg
• Flash Point: 288 °C
• Appearance: Brown solid
• Density: 1.354 g/cm³
• Vapor Pressure: 8.09E-13mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER(519032-08-7)
• EPA Substance Registry System: 4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER(519032-08-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 519032-08-7(Hazardous Substances Data)

Usage

Chemical Properties

Brown Solid

Uses

An intermediate in the preparation of HIV-integrase inhibitors

InChI:InChI=1/C17H19N3O6/c1-17(2,20-16(24)26-9-10-7-5-4-6-8-10)15-18-11(14(23)25-3)12(21)13(22)19-15/h4-8,21H,9H2,1-3H3,(H,20,24)(H,18,19,22)

Upstream product

• 518047-98-8 [1-(N'-hydroxycarbamimidoyl)-1-methyl-ethyl]carbamic acid benzyl ester 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 1064707-10-3 C₁₈H₂₃N₃O₇ 
• 501-53-1 benzyl chloroformate 
• 100134-82-5 (cyano-dimethyl-methyl)carbamic acid benzyl ester 
• 518047-98-8 benzyl [2-amino-2-(hydroxyimino)-1,1-dimethylethyl]carbamate 
• 1064707-10-3 2-[(2-benzyloxycarbonylamino-2-methyl-propionimidoyl)-aminooxy]-but-2-enedioic acid dimethyl ester 

Downstream Products

• 518048-00-5 methyl 5-(benzoyloxy)-2-(1-{[(benzyloxy)carbonyl]amino}-1-methylethyl)-6-hydroxypyrimidine-4-carboxylate 
• 1415000-05-3 C₂₃H₂₄N₄O₅ 
• 1415000-06-4 C₂₃H₂₃ClN₄O₅ 
• 1415000-07-5 C₂₄H₂₆N₄O₅ 
• 1415000-08-6 C₂₄H₂₃F₃N₄O₅ 
• 1415000-09-7 C₂₄H₂₆N₄O₆ 
• 1415000-10-0 C₂₆H₃₀N₄O₈ 
• 1415000-11-1 C₂₄H₂₅FN₄O₅ 
• 1415000-12-2 C₂₄H₂₆N₄O₅ 
• 1415000-13-3 benzyl 2-(4-(2-(1H-indol-2-yl)ethylcarbamoyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-ylcarbamate 
• 1415000-17-7 C₁₆H₁₉N₅O₅ 
• 1415000-14-4 benzyl 2-(5-hydroxy-4-(2-methoxyethylcarbamoyl)-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-ylcarbamate 
• 1415000-15-5 benzyl 2-(5-hydroxy-4-(3-methoxypropylcarbamoyl)-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-ylcarbamate 
• 1415000-16-6 benzyl 2-(4-(cyclopropylmethylcarbamoyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-ylcarbamate 

Relevant articles and documents

Structural modifications of 5,6-dihydroxypyrimidines with anti-HIV activity

A series of 5,6-dihydroxypyrimidine analogs were synthesized and evaluated for their anti-HIV activity in vitro. Among all of the analogs, several compounds exhibited significant anti-HIV activity, especially 1b and 1e, which showed the most potent anti-HIV activity with EC50 values of 0.14 and 0.15 μM, and TI (therapeutic index) values of >300 and >900, respectively. Further docking studies revealed that the representative compounds 1e and 3a could meet the HIV-1 integrase inhibition minimal requirements of a chelating domain (two metal ions) and an aromatic domain (π-π stacking interactions).

Dihydroxypyrimidine-4-carboxamides as novel potent and selective HIV integrase inhibitors

Human immunodeficiency virus type-1 (HIV-1) integrase, one of the three constitutive viral enzymes required for replication, is a rational target for chemotherapeutic intervention in the treatment of AIDS that has also recently been confirmed in the clinical setting. We report here on the design and synthesis of N-benzyl-5,6-dihydroxypyrimidine-4-carboxamides as a class of agents which exhibits potent inhibition of the HIV-integrase-catalyzed strand transfer process. In the current study, structural modifications on these molecules were made in order to examine effects on HIV-integrase inhibitory potencies. One of the most interesting compounds for this series is 2-[1-(dimethylamino)-1-methylethyl]-N-(4-fluorobenzyl)-5,6-dihydroxypyrimidine- 4-carboxamide 38, with a CIC95 of 78 nM in the cell-based assay in the presence of serum proteins. The compound has favorable pharmacokinetic properties in preclinical species (rats, dogs, and monkeys) and shows no liabilities in several counterscreening assays, highlighting its potential as a clinically useful antiviral agent.