ChemicalBook CAS DataBase List 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile

4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile synthesis

5synthesis methods

Product Name:4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile
CAS Number:500287-72-9
Molecular formula:C22H18N6
Molecular Weight:366.42

Rilpivirine is a pharmaceutical drug, developed by Tibotec, for the treatment of HIV infection. It is a second-generation non-nucleoside reverse transcriptase inhibitor (NNRTI) with higher potency, longer half-life and reduced side-effect profile compared with older NNRTIs, such as efavirenz. Rilpivirine entered phase III clinical trials in April 2008, and was approved for use in the United States in May 2011. A fixed-dose drug combining rilpivirine with emtricitabine and tenofovir, was approved by the U.S. Food and Drug Administration in August 2011 under the brand name Complera.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

Guillemont, Jerome; Pasquier, Elisabeth; Palandjian, Patrice; Vernier, Daniel; Gaurrand, Sandrine; Lewi, Paul J.; Heeres, Jan; de Jonge, Marc R.; Koymans, Lucien M. H.; Daeyaert, Frits F. D.; Vinkers, Maarten H.; Arnold, Edward; Das, Kalyan; Pauwels, Rudi; Andries, Koen; de Bethune, Marie-Pierre; Bettens, Eva; Hertogs, Kurt; Wigerinck, Piet; Timmerman, Philip; Janssen, Paul A. J. Synthesis of novel diarylpyrimidine analogues and their antiviral activity against human immunodeficiency virus type 1. Journal of Medicinal Chemistry. Volume 48. Issue 6. Pages 2072-2079. Journal. (2005).

3-{4-[2-(4-Cyano-phenylamino)-1-oxy-pyrimidin-4-ylamino]-3,5-dimethyl-phenyl}-acrylamide

500288-66-4
16 suppliers
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4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile

500287-72-9
265 suppliers
$12.00/1mg

Yield:500287-72-9 93.9%

Reaction Conditions:

with trichlorophosphate at 20;Reflux;

Steps:

3 Synthesis of compound V:

Add compound VI (10.00g, 26.0mmoL) and 80ml phosphorous oxychloride as solvent in a 500mL three-necked flask. Stir for 2-3h at 20-30, then heat to reflux for 3h. TLC tracked until the compound VI remained unchanged, the temperature was lowered to 5-10°C, the stirring was continued for 1 h, and then suction filtered and dried to obtain 9.05 g of a light yellow solid, which was the crude compound V, with a yield of 95.0%. Add all the above-mentioned light yellow solids into a 500ml three-necked flask containing 300ml of acetone, heat it to clear, and then add 0.8g of activated carbon. Incubate and stir for 1 hour. After filtering while hot, the filtrate is spin-dried to obtain 8.50 g of a white solid, which is a pure product of compound V, with a purity of 99.74% and a yield of 93.9%.

References:

CN112010810,2020,A Location in patent:Paragraph 0034; 0067-0070

(E)-3-(4-((2-chloropyrimidin-4-yl)amino)-3,5-dimethylphenyl)acrylonitrile

1538550-43-4
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873-74-5
657 suppliers
$9.00/1g

500287-72-9
265 suppliers
$12.00/1mg

References

2-Propenenitrile, 3-(4-amino-3,5-dimethylphenyl)-, hydrochloride (1:1)

500292-90-0
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4-[(4-CHLORO-2-PYRIMIDINYL)AMINO]BENZONITRILE

244768-32-9
176 suppliers
$69.00/1/ G

500287-72-9
265 suppliers
$12.00/1mg

References

500292-94-4 Synthesis

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

500292-94-4
42 suppliers
inquiry

244768-32-9
176 suppliers
$69.00/1/ G

500287-72-9
265 suppliers
$12.00/1mg

References

244768-32-9
176 suppliers
$69.00/1/ G

500287-72-9
265 suppliers
$12.00/1mg

References

4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile Related Search:

Darunavir ethanolate Etravirine Raltegravir Nevirapine Lapatinib Abacavir Efavirenz Ritonavir Zidovudine DAPIVIRINE,4-[[4-(2,4,6-TRIMETHYLPHENYL)AMINO]PYRIMIDIN-2-YL]AMINO]BENZONITRILE