62222-36-0

Usage

Uses

Used in Pharmaceutical Industry:
5,6-Dihydroxy-2-phenyl-pyrimidine-4-carboxylic acid methyl ester is used as a key intermediate in the synthesis of various pharmaceuticals. Its presence in the molecular structure allows for the development of new compounds with potential therapeutic applications, making it an essential component in drug discovery and design.
Used in Agrochemical Industry:
In the agrochemical industry, 5,6-Dihydroxy-2-phenyl-pyrimidine-4-carboxylic acid methyl ester serves as an intermediate in the preparation of new pesticides and herbicides. Its unique chemical structure contributes to the development of innovative and effective agrochemicals, enhancing crop protection and yield.
Used in Organic Synthesis:
5,6-Dihydroxy-2-phenyl-pyrimidine-4-carboxylic acid methyl ester is used as a versatile building block in organic synthesis. Its presence in the molecular structure allows for the creation of a wide range of compounds with diverse applications, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique properties make it an invaluable resource for chemists and researchers in the field of organic synthesis.

Upstream product

• 1422555-43-8 C₁₃H₁₄N₂O₅ 
• 100-47-0 benzonitrile 
• 33229-29-7 C₁₃H₁₄N₂O₅ 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 613-92-3 (E)-N'-hydroxybenzimidamide 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 613-92-3 N-hydroxyl-benzamidine 
• 33229-29-7 (E)-2-(Benzimidoyl-aminooxy)-but-2-enedioic acid dimethyl ester 

Downstream Products

• 62222-38-2 5,6-dihydroxy-2-phenyl-pyrimidine-4-carboxylic acid 
• 1407174-91-7 N-(cyclohexylmethyl)-5,6-dihydroxy-2-phenylpyrimidine-4-carboxamide 

Relevant academic research and scientific papers

Pharmacophore requirements for HIV-1 reverse transcriptase inhibitors that selectively “Freeze” the pre-translocated complex during the polymerization catalytic cycle

Reverse transcriptase (RT) is responsible for replicating the HIV-1 genome and is a validated therapeutic target for the treatment of HIV infections. During each cycle of the RT-catalyzed DNA polymerization process, inorganic pyrophosphate is released as the by-product of nucleotide incorporation. Small molecules were identified that act as bioisosteres of pyrophosphate and can selectively freeze the catalytic cycle of HIV-1 RT at the pre-translocated stage of the DNA- or RNA-template-primer-enzyme complex.

Design and discovery of 5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxamide inhibitors of HIV-1 integrase

Raltegravir (RAL) is a first clinically approved integrase (IN) inhibitor for the treatment of HIV but rapid mutation of the virus has led to chemo-resistant strains. Therefore, there is a medical need to develop new IN inhibitors to overcome drug resista

Rapid catalyst identification for the synthesis of the pyrimidinone core of HIV integrase inhibitors

A microscale chemistry improvement engine: A pre-dosed microscale high-throughput experimentation additives platform enables rapid, serendipitous reaction improvement. This platform allowed one chemist to set up 475 experiments and analyze the results using MISER chromatography in a single day, thus resulting in two high-quality catalytic systems for the construction of the title compound 1. Support for a single-electron transfer mechanism was obtained. Copyright

RNase H active site inhibitors of human immunodeficiency virus type 1 reverse transcriptase: Design, biochemical activity, and structural information

Pyrimidinol carboxylic acids were designed as inhibitors of HIV-1 RNase H function. These molecules can coordinate to two divalent metal ions in the RNase H active site. Inhibition of enzymatic activity was measured in a biochemical assay, but no antivira

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.

4,5-Dihydroxypyrimidine carboxamides and N-alkyl-5-hydroxypyrimidinone carboxamides are potent, selective HIV integrase inhibitors with good pharmacokinetic profiles in preclinical species

The dihydroxypyrimidine carboxamide 4a was discovered as a potent and selective HIV integrase strand transfer inhibitor. The optimization of physicochemical properties, pharmacokinetic profiles, and potency led to the identification of 13 in the dihydroxypyrimidine series and 18 in the N-methylpyrimidinone series having low nanomolar activity in the cellular HIV spread assay in the presence of 50% normal human serum and very good pharmacokinetics in preclinical species.

Efficient synthesis of functionalized pyrimidones via microwave-accelerated rearrangement reaction

An efficient synthesis of functionalized pyrimidones via microwave-accelerated rearrangement reaction of amidoxime DMAD adducts is described. In most cases, the pyrimidone formation was furnished in reasonable yield after 2 min of microwave irradiation.