189956-45-4

Basic information

• Product Name: 4-N[2(4-HYDROXYPYRIMIDINYL)]AMINOBENZONITRILE
• Synonyms: 4-((4-Oxo-1,4-dihydropyriMidin-2-yl)aMino)benzonitrile;Benzonitrile, 4-[(1,4-dihydro-4-oxo-2-pyriMidinyl)aMino]-;4-[(4-Hydroxy-pyrimidin-2-yl)amino]-benzonitr;4-[(6-oxo-1H-pyrimidin-2-yl)amino]benzonitrile;4-((4-Oxo-1,4-dihydropyrimidin-2-yl);4-N[2(4-HYDROXYPYRIMIDINYL)]AMINOBENZONITRILE;4-[(1,4-Dihydro-4-oxo-2-pyrimidinyl)amino]benzonitrile;4-[(4-Hydroxy-2-pyrimidinyl)amino]benzonitrile
• CAS NO: 189956-45-4
• Molecular Formula: C₁₁H₈N₄O
• Molecular Weight: 212.21
• Product Categories: Intermediate of Etravirine;pharmacetical
• Mol File: 189956-45-4.mol

Chemical Properties

• Boiling Point: 399.7 °C at 760mmHg
• Flash Point: 195.6 °C
• Appearance: /
• Density: 1.31 g/cm³
• Vapor Pressure: 1.34E-06mmHg at 25°C
• Refractive Index: 1.67
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.66±0.40(Predicted)
• CAS DataBase Reference: 4-N[2(4-HYDROXYPYRIMIDINYL)]AMINOBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-N[2(4-HYDROXYPYRIMIDINYL)]AMINOBENZONITRILE(189956-45-4)
• EPA Substance Registry System: 4-N[2(4-HYDROXYPYRIMIDINYL)]AMINOBENZONITRILE(189956-45-4)

Safety Data

• Hazardous Substances Data: 189956-45-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-N[2(4-HYDROXYPYRIMIDINYL)]AMINOBENZONITRILE is used as a chemical intermediate for the preparation of 2-naphthyl substituted diarylpyrimidines (DAPY) analogues, which are of interest in the development of new pharmaceutical compounds. The synthesis of these DAPY analogues allows for the exploration of their potential therapeutic properties and applications in treating various medical conditions.
Used in Chemical Research:
4-N[2(4-HYDROXYPYRIMIDINYL)]AMINOBENZONITRILE is also used as a research compound in the field of organic chemistry. Its unique structure and properties make it a valuable tool for studying the synthesis and reactivity of related compounds, as well as for investigating the potential applications of DAPY analogues in various industries.

InChI:InChI=1/C11H8N4O/c12-7-8-1-3-9(4-2-8)14-11-13-6-5-10(16)15-11/h1-6H,(H2,13,14,15,16)

Upstream product

• 5751-20-2 2-(methylsulfanyl)pyrimidin-4-ol 
• 873-74-5 4-Aminobenzonitrile 
• 1228671-28-0 4-((4-methoxypyrimidin-2-yl)amino)benzonitrile 
• 924-99-2 ethyl 3-(dimethylamino)acrylate 
• 5637-42-3 1-(4-cyanophenyl)guanidine 
• 999-59-7 methyl 3-(N,N-dimethylamino)-2-propenoate 
• 5751-20-2 2-Methylthiouracil 

Downstream Products

• 500287-72-9 rilpivirine 
• 700361-47-3 Rilpivirine hydrochloride 
• 269055-46-1 4-[[5-bromo-6-[(4-cyano-2,6-dimethylphenyl)amino]-2-pyrimidinyl]-amino]benzonitrile 
• 269055-04-1 4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-2-pyrimidinyl]-amino]benzonitrile 
• 269055-22-3 4-[5-bromo-4-(2,4,6-trimethyl-phenoxy)-pyrimidin-2-ylamino]-benzonitrile 
• 244767-99-5 4-((2-((4-cyanophenyl)amino)pyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile 

Relevant articles and documents

Industrial synthesis method of rilpivirine and intermediate compound

The invention discloses an industrial synthesis method of rilpivirine. A compound as shown in a formula I and compound hydrochloride as shown in a formula VI react to obtain rilpivirine. The invention further discloses an intermediate compound as shown in the formula I and a synthesis method of the intermediate compound. Compared with the prior art, the synthesis method is simple to operate, mild in condition, high in yield and purity and suitable for industrial production.

Pyrimidine heterocyclic compounds, pyrimidine heterocyclic compound salts, and preparation method and application thereof

The invention provides pyrimidine heterocyclic compounds, pyrimidine heterocyclic compound salts, and a preparation method and application thereof. According to the pyrimidine heterocyclic compounds provided by the invention, specific Rq is selected, so that the obtained compounds have favorable drug resistance and long half life when being used as the medicine for treating or preventing HIV. The compounds have the advantages of high activity, low toxicity and high stability.

4-[ (4-chloro-2-pyrimidinyl) amino] phenyl nitrile preparation method

The invention discloses a new preparation method of 4-[(4-chlorine-2-pyrimidyl)amino] cyanophenyl. The preparation method comprises the steps of carrying out a reaction on N-guanidine cyanophenyl and NN,-dimethyl amino acrylate to generate II, and then carrying out chlorination on equivalent phosphorus oxychloride to generate a target product. By adopting the preparation method, the yield and the quality of the product can be improved; the cost is reduced, and the method is simple and convenient to operate, and suitable for a synthetic route of rilpivirine bodbody in industrial production.

RILPIVIRINE PROCESS

Disclosed is process for the preparation of a key Rilpivirine intermediate namely, (E)-4-(2-cyanoethenyl)-2,6-dimethylphenylamine hydrochloride (II) by a process comprising reaction of the tetrafluoroborate salt of the diazonium ion of 2,6-dimethyl-4-amin

PROCESS FOR RILPIVIRINE

The present invention provides a novel process for the preparation of 4-(4-hydroxypyrimidin-2-ylamino)benzonitrile. The present invention also provides a novel process for the preparation of 4-iodo-2,6-dimethyl benzenamine. The present invention further provides an improved process for the preparation of rilpivirine. The present invention further provides a tosylate salt of rilpivirine, process for its preparation and pharmaceutical compositions comprising it.

RILPIVIRINE HYDROCHLORIDE

The present invention provides a novel process for the preparation of rilpivirine. The present invention also provides a novel process for the preparation of rilpivirine hydrochloride. The present invention further provides a rilpivirine hydrochloride monohydrate, process for its preparation and pharmaceutical compositions comprising it.

RILPIVIRINE HYDROCHLORIDE

As used herein the term "room temperature" refers to a temperature of about 25°C to about 35°C. According to one aspect of the present invention, there IS provided a novel process for the preparation of rilpivirine, which comprises: a) condensing the (E)-3-( 4-amino-3,5-dimethylphenyl)acrylonitrile hydrochloride with 4-( 4-chloropyrimidin-2-ylamino )benzonitrile m the presence of Nmethylpyrrolidone; b) heating the contents obtained in step (a) at about 75 to 95°C to obtain a solution; c) cooling the solution obtained in step (b) at below 35°C; d) adding water to the reaction mass; and e) isolating rilpivirine. The reaction in step (b) may preferably be heated to 100 to 110°C. Step (c) may preferably be carried out at room temperature. Rilpivirine may be isolated in step (e) by the methods known such as Filtration or centrifugation.

PROCESS FOR RILPIVIRINE

The present invention provides a novel process for the preparation of 4-(4-hydroxypyrimidin-2-ylamino)benzonitrile. The present invention also provides a novel process for the preparation of 4-iodo-2,6-dimethyl benzenamine. The present invention further provides an improved process for the preparation of rilpivirine. The present invention further provides a tosylate salt of rilpivirine, process for its preparation and pharmaceutical compositions comprising it.

Evolution of anti-HIV drug candidates. Part 3: Diarylpyrimidine (DAPY) analogues

The synthesis and anti-HIV-1 activity of a series of diarylpyrimidines (DAPYs) are described. Several members of this novel class of non-nucleoside reverse transcriptase inhibitors (NNRTIs) are extremely potent against both wild-type and a panel of clinically significant single- and double-mutant strains of HIV-1.