Rilpivirine-d6

Base Information

• Chemical Name: Rilpivirine-d6
• CAS No.: 1312424-26-2
• Molecular Formula: C22H18N6
• Molecular Weight: 366.41852
• DSSTox Substance ID: DTXSID10692874
• Mol file: 1312424-26-2.mol

Synonyms:Rilpivirine-d6;1312424-26-2;4-[[4-[4-[(E)-2-cyanoethenyl]-2,6-bis(trideuteriomethyl)anilino]pyrimidin-2-yl]amino]benzonitrile;Rilpivirine D6;DTXSID10692874;HY-10574S;CS-O-06927;CS-0202016;4-[(4-{4-[(E)-2-Cyanoethenyl]-2,6-bis[(~2~H_3_)methyl]anilino}pyrimidin-2-yl)amino]benzonitrile

Chemical Property of Rilpivirine-d6

Chemical Property:

• PSA: 100.65000
• LogP: 4.48396
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly, Heated), Methanol (Sparingly)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 372.19695508
• Heavy Atom Count: 28
• Complexity: 607

Purity/Quality:

97% ^*data from raw suppliers

Rilpivirine-d6 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C)C=CC#N
• Isomeric SMILES: [2H]C([2H])([2H])C1=CC(=CC(=C1NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C([2H])([2H])[2H])/C=C/C#N
• Uses: Labeled Rilpivirine, intended for use as an internal standard for the quantification of Rilpivirine by GC- or LC-mass spectrometry. A labelled novel non-nucleoside reverse transcriptase inhibitor. Rilpivirine seems to be well tolerated with less CNS disturbance than Efavirenz, and has non-teratogenic potential. An anti-HIV agent. Rilpivirine-d6 is a labelled novel non-nucleoside reverse transcriptase inhibitor. Rilpivirine-d6 seems to be well tolerated with less CNS disturbance than Efavirenz, and has non-teratogenic potential.

Technology Process of Rilpivirine-d6

There total 4 articles about Rilpivirine-d6 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: 64.0%

(E)-3-(4-amino-3,5-dimethylphenyl)acrylonitrile-d6 (1795135-93-1) + 4-[(4-chloro-2-pyrimidinyl)amino]benzonitrile (244768-32-9) → (E)-4-((4-((4-(2-cyanovinyl)-2,6-dimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile-d6 (1312424-26-2)

Guidance literature:

In acetonitrile; for 72h; Reflux;

Reference yield:

2,6-dimethylaniline (87-62-7) → (E)-4-((4-((4-(2-cyanovinyl)-2,6-dimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile-d6 (1312424-26-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: d⁽⁴⁾-methanol; water-d2; sodium formate / palladium on activated charcoal / 160 °C

2.1: Iodine monochloride; sodium hydrogencarbonate / methanol; dichloromethane / 0.67 h

3.1: sodium acetate / palladium on activated charcoal / N,N-dimethyl acetamide / 130 °C

3.2: 0.5 h / 60 °C

4.1: acetonitrile / 72 h / Reflux

With d⁽⁴⁾-methanol; water-d2; sodium formate; sodium acetate; Iodine monochloride; sodium hydrogencarbonate; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl acetamide; acetonitrile; 3.1: Heck cross coupling;

Reference yield:

d7-2,6-dimethylaniline (1092804-96-0) → (E)-4-((4-((4-(2-cyanovinyl)-2,6-dimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile-d6 (1312424-26-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Iodine monochloride; sodium hydrogencarbonate / methanol; dichloromethane / 0.67 h

2.1: sodium acetate / palladium on activated charcoal / N,N-dimethyl acetamide / 130 °C

2.2: 0.5 h / 60 °C

3.1: acetonitrile / 72 h / Reflux

With sodium acetate; Iodine monochloride; sodium hydrogencarbonate; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl acetamide; acetonitrile; 2.1: Heck cross coupling;

upstream raw materials:

2,6-dimethylaniline

(E)-3-(4-amino-3,5-dimethylphenyl)acrylonitrile-d6

4-[(4-chloro-2-pyrimidinyl)amino]benzonitrile

d7-2,6-dimethylaniline

Refernces