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Simagchem Corporation

Welcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our

High quality Etravirine supplier in China

Cas:269055-15-4

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

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Ality Chemical Corporation

The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi

Factory Supply Etravirine

Cas:269055-15-4

Min.Order:1

Negotiable

Type:Other

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Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

We can provide GMP validation service that complies with SFDA, FDA, WHO and EU EMPA.Excellent registration team could help us easlily to register our products in different countries.If you and your customer are interested in some products or need C

Etravirine manufacturer with low price

Cas:269055-15-4

Min.Order:1 Gram

Negotiable

Type:Manufacturers

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Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

Factory Price API 99% Etravirine 269055-15-4 GMP Manufacturer

Cas:269055-15-4

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

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Dayang Chem (Hangzhou) Co.,Ltd.

DayangChem exported this product to many countries and regions at best price. If you are looking for the material's manufacturer or supplier in China, DayangChem is your best choice. Pls contact with us freely for getting detailed product spe

Etravirine Manufacturer/High quality/Best price/In stock

Cas:269055-15-4

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

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Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

Etravirine

Cas:269055-15-4

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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Hebei yanxi chemical co.,LTD.

chengdu and import and export trade co., LTD., who registered capital of 10 million yuan, nearly to $2 million, we have a pharmaceutical raw materials factory production of pharmaceutical raw materials, and a reagent r&d center, and we do res

etravirine

Cas:269055-15-4

Min.Order:1000 Gram

FOB Price: $500.0

Type:Trading Company

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Hebei Nengqian Chemical Import and Export Co., LTD

Our advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva

Etravirine In stock

Cas:269055-15-4

Min.Order:1 Gram

FOB Price: $1000.0 / 1300.0

Type:Trading Company

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Henan Tianfu Chemical Co., Ltd.

Henan Tianfu Chemical Co., Ltd. is located in Zhengzhou High-tech Development Zone with import and export license. We passed ISO 9001:2008 in 2009, and won "High-tech Enterprise" by provincial government in 2013.The objective of the com

TIANFU-CHEM - 4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3, 5 –dimethylbenzonitrile

Cas:269055-15-4

Min.Order:1 Gram

FOB Price: $1000.0

Type:Lab/Research institutions

inquiry

Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

BP StandardCAS 269055-15-4 with competitive price

Cas:269055-15-4

Min.Order:10 Gram

FOB Price: $146.0 / 176.0

Type:Trading Company

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Wuhan Han Sheng New Material Technology Co.,Ltd

Our Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We

Hot Sell Factory Supply Raw Material Etravirine CAS NO.269055-15-4

Cas:269055-15-4

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

inquiry

Hebei Sankai Chemical Technology Co., Ltd

1. Product advantages ♦ High purity, all above 98.5%, no impurities after dissolution ♦ We will test each batch to ensure quality ♦ OEM and private brand services designed for free ♦ Various cap colors available ♦ W

4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3, 5 –dimethylbenzonitrile CAS269055-15-4

Cas:269055-15-4

Min.Order:1 Kilogram

FOB Price: $7.0 / 9.0

Type:Trading Company

inquiry

Henan Sinotech Import&Export Corporation

Product Name: Etravirine Molecular Formula C20H15BrN6O CAS Number 269055-15-4 Appearance:White powder Storage:Store in cool and dry place, away from sun light. Package:25kg/drum Application:Syntheses Material Intermediates Transportation:By sea

Etravirine

Cas:269055-15-4

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Other

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Hubei Langyou International Trading Co., Ltd

Advantages: Hubei XinRunde Chemical Co., Ltd is a renowned pharmaceutical manufacturer. We can offer high quality products at competitive price in quick delivery with 100% custom pass guaranteed. Never stop striving to offer our best service is

99%min TMC 125 Manufacturer

Cas:269055-15-4

Min.Order:10 Gram

Negotiable

Type:Other

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HANWAYS CHEMPHARM CO.,LIMITED

Hanways chempharm is a specialized company concentrating on the R&D, production, marketing and technical service of APIs and pharmaceutical intermediates. The marketing department is located in Wuhan. We have two GMP facilities in Hubei Pr

Organic Chemical Etravirine Tmc-125 CAS 269055-15-4 for Treating HIV

Cas:269055-15-4

Min.Order:1 Kilogram

FOB Price: $200.0 / 400.0

Type:Trading Company

inquiry

Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized

Etravirine 269055-15-4

Cas:269055-15-4

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Baoji Guokang Healthchem co.,ltd

Our company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At prese

Qingdao Beluga Import and Export Co., LTD

Etravirine CAS:269055-15-4 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediate

Etravirine CAS:269055-15-4

Cas:269055-15-4

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

Etravirine

Cas:269055-15-4

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

LIDE PHARMACEUTICALS LIMITED

Advantage : LIDE PHARMACEUTICALS LTD. is a mid-small manufacturing-type enterprise, engaged in pharmaceutical intermediates of R&D, custom-made and production, and also involving trading chemicals for export. We have established the R&amp

Etravirine/ LIDE PHARMA- Factory supply / Best price

Cas:269055-15-4

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Lonwin Chemical Group Limited

4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3, 5 –dimethylbenzonitrile CAS: 269055-15-4 Specification Item Standard Structural data confirmation 1. H-NMR: The data of str

Hebei Quanhe Biotechnology Co. LTD

1. Timely and efficient service to ensure communication with customers 2. Produce products of different specifications and sizes according to your requirements. 3. Quality procedures and standards recognized by SGS. Advanced plant equipment ensures s

4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3, 5 –dimethylbenzonitrile

Cas:269055-15-4

Min.Order:1 Kilogram

FOB Price: $10.0 / 100.0

Type:Lab/Research institutions

inquiry

Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

Etravirine

Cas:269055-15-4

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Afine Chemicals Limited

Our Services 1. New Molecules R&D 2. Own test center HPLC NMR GC LC-MS 3. API and Intermediates from China reputed manufacturers 4. Documents support COA MOA MSDS DMF open part Our advantages 1. Government awarded company. Top 100 enter

Etravirine

Cas:269055-15-4

Min.Order:1 Kilogram

FOB Price: $1.0 / 100000.0

Type:Lab/Research institutions

inquiry

Taizhou Crene Biotechnology co.ltd

Our company provides one-stop services of research - development - production for a variety of special prouducts. Not only do we make effective use of our strong technological strength, but also establish of cooperative relations with several well-

TMC-125 Etravirine 269055-15-4

Cas:269055-15-4

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Fonlynn Health Technology Co., Ltd.

Packing: According to customer requirements Delivery time: In stock or depands Port of shipment: Ningbo/Shanghai/Qingdao OEM/ODM:Welcome Sample:We can offer our existing samples at once Transportation:Express/Sea/Air Port:Ningbo/Shanghai/Qingd

Etravirine

Cas:269055-15-4

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Hangzhou Lingrui Chemical Co.,Ltd.

advantage: 1. The best price, satisfactory quality; 2. customers have the right to choose the delivery of parcels (EMS, DHL, FedEx, UPS); 3. customers have the right to choose from the recent effective packaging methods of their products packaging

Best price/In stock Etravirine 269055-15-4

Cas:269055-15-4

Min.Order:1 Gram

Negotiable

Type:Other

inquiry

Hangzhou J&H Chemical Co., Ltd.

J&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia

Etravirine

Cas:269055-15-4

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

Etravirine/TMC125/Intelence

Cas:269055-15-4

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

SHANGHAI SYSTEAM BIOCHEM CO., LTD

We are one of a few suppliers that can offer custom synthesis service of this product We are specialized in custom synthesis, chemical/pharmaceutical/ pesticides outsourcing and contract research. We are committed to prov

Etravirine CAS NO.269055-15-4

Cas:269055-15-4

Min.Order:100 Gram

FOB Price: $100.0 / 2000.0

Type:Lab/Research institutions

inquiry

Synthetic route

4-{6-amino-2-[(4-cyanophenyl)amino]pyrimidin-4-yloxy}-3,5-dimethylbenzenecarbonitrile

4-{6-amino-2-[(4-cyanophenyl)amino]pyrimidin-4-yloxy}-3,5-dimethylbenzenecarbonitrile

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Stage #1: 4-{6-amino-2-[(4-cyanophenyl)amino]pyrimidin-4-yloxy}-3,5-dimethylbenzenecarbonitrile With bromine In propan-1-ol at 5 - 20℃;
Stage #2: With sodium hydroxide In propan-1-ol; water at 0 - 20℃; Product distribution / selectivity;
92.82%
With bromine In dichloromethane at 0 - 5℃; for 4h;80%
With bromine In dichloromethane at 0 - 5℃; for 5h;80.2%
4-((4-amino-5-bromo-6-chloropyrimidin-2-yl)amino)benzonitrile
1398507-09-9

4-((4-amino-5-bromo-6-chloropyrimidin-2-yl)amino)benzonitrile

3,5-dimethyl-4-hydroxybenzonitrile
4198-90-7

3,5-dimethyl-4-hydroxybenzonitrile

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Stage #1: 3,5-dimethyl-4-hydroxybenzonitrile With potassium carbonate; potassium iodide In 1-methyl-pyrrolidin-2-one at 0 - 5℃; for 0.166667h; Inert atmosphere;
Stage #2: 4-((4-amino-5-bromo-6-chloropyrimidin-2-yl)amino)benzonitrile In 1-methyl-pyrrolidin-2-one at 10 - 120℃; for 26.5h; Time; Temperature; Reagent/catalyst; Concentration; Inert atmosphere;
89%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 12h; Inert atmosphere;10 g
C25H22BrN5O3
1616667-63-0

C25H22BrN5O3

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Stage #1: C25H22BrN5O3 With silver(II) fluoride Inert atmosphere; Glovebox;
Stage #2: With ammonia In water; isopropyl alcohol at 80℃; for 0.5h;
Stage #3: With hydrogenchloride In water at 0.25℃; for 0.5h;
56%
4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-6-chloro-2-pyrimidinyl]amino]-benzonitrile
269055-76-7

4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-6-chloro-2-pyrimidinyl]amino]-benzonitrile

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
With ammonia In isopropyl alcohol41%
In water40.5%
In water40.5%
With ammonia In 1,4-dioxane at 150℃; for 96h; Sealed tube;0.44 g
4-((4,6-dichloropyrimidin-2-yl)amino)benzonitrile
329187-59-9

4-((4,6-dichloropyrimidin-2-yl)amino)benzonitrile

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 78 percent / Br2; NaHCO3 / H2O; methanol
2: 45 percent / N-methylpyrrolidine / dioxane
3: 41 percent / NH3 / propan-2-ol
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 45 °C
2.1: ammonia / 1,4-dioxane; water / 12 h / 120 °C
3.1: bromine / dichloromethane / 4 h / 0 - 5 °C
3.2: pH 9 - 10
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 45 °C
2.1: ammonium hydroxide / water; 1,4-dioxane / 12 h / 120 °C
3.1: bromine / dichloromethane / 4 h / 0 - 5 °C
3.2: pH 9-10
View Scheme
Multi-step reaction with 3 steps
1: N-Bromosuccinimide / tetrahydrofuran / 20 °C
2: ammonia / 1,4-dioxane / 1 h / 50 °C / Sealed tube
3: potassium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 80 °C / Inert atmosphere
View Scheme
4-((4,6-dihydroxypyrimidine-2-yl)amino)benzonitrile
374067-80-8

4-((4,6-dihydroxypyrimidine-2-yl)amino)benzonitrile

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 86 percent / POCl3
2: 78 percent / Br2; NaHCO3 / H2O; methanol
3: 45 percent / N-methylpyrrolidine / dioxane
4: 41 percent / NH3 / propan-2-ol
View Scheme
Multi-step reaction with 4 steps
1.1: trichlorophosphate; N,N-dimethyl-aniline / 6 h / Reflux
2.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 45 °C
3.1: ammonia / 1,4-dioxane; water / 12 h / 120 °C
4.1: bromine / dichloromethane / 4 h / 0 - 5 °C
4.2: pH 9 - 10
View Scheme
Multi-step reaction with 4 steps
1.1: trichlorophosphate; N,N-dimethyl-aniline / 6 h / Reflux
2.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 45 °C
3.1: ammonium hydroxide / water; 1,4-dioxane / 12 h / 120 °C
4.1: bromine / dichloromethane / 4 h / 0 - 5 °C
4.2: pH 9-10
View Scheme
Multi-step reaction with 4 steps
1: trichlorophosphate / 12 h / 90 - 95 °C
2: N-Bromosuccinimide / tetrahydrofuran / 20 °C
3: ammonia / 1,4-dioxane / 1 h / 50 °C / Sealed tube
4: potassium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 80 °C / Inert atmosphere
View Scheme
4-[[(5-bromo-4,6-dichloro)-2-pyrimidinyl]amino]benzonitrile
269055-75-6

4-[[(5-bromo-4,6-dichloro)-2-pyrimidinyl]amino]benzonitrile

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 45 percent / N-methylpyrrolidine / dioxane
2: 41 percent / NH3 / propan-2-ol
View Scheme
4-cyanophenyl guanidine hydrochloride

4-cyanophenyl guanidine hydrochloride

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 76 percent / NaOEt / ethanol
2: 86 percent / POCl3
3: 78 percent / Br2; NaHCO3 / H2O; methanol
4: 45 percent / N-methylpyrrolidine / dioxane
5: 41 percent / NH3 / propan-2-ol
View Scheme
4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile hydrobromide
1030633-38-5

4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile hydrobromide

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 1.25h;
4-{6-amino-2-[(4-cyanophenyl)amino]pyrimidin-4-yloxy}-3,5-dimethylbenzenecarbonitrile

4-{6-amino-2-[(4-cyanophenyl)amino]pyrimidin-4-yloxy}-3,5-dimethylbenzenecarbonitrile

A

4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile hydrobromide
1030633-38-5

4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile hydrobromide

B

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Stage #1: 4-{6-amino-2-[(4-cyanophenyl)amino]pyrimidin-4-yloxy}-3,5-dimethylbenzenecarbonitrile With bromine; acetic acid at 20 - 80℃; for 4.25h;
Stage #2: With sodium hydroxide In water at 20℃;
etravirine phosphate
1253183-22-0

etravirine phosphate

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 0.5h;
etravirine tosylatee salt
1030633-41-0

etravirine tosylatee salt

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
With sodium hydroxide In water at 0 - 20℃; for 1.75h; Product distribution / selectivity;
3,5-dimethyl-4-hydroxybenzonitrile
4198-90-7

3,5-dimethyl-4-hydroxybenzonitrile

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water; acetone / 3 - 30 °C
1.2: 0.17 h / 10 °C / Inert atmosphere
1.3: 2 h / 10 °C
2.1: ammonia / 1-methyl-pyrrolidin-2-one; water / 19 h / 120 °C
3.1: bromine / propan-1-ol / 5 - 20 °C
3.2: 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 2 h / 70 °C / Large scale reaction
2: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 2 h / 0 - 5 °C / Large scale reaction
3: ammonia / 1,4-dioxane; water / 12 h / 120 °C / Autoclave; Large scale reaction
4: bromine / dichloromethane / 4 h / 0 - 5 °C
View Scheme
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 70 °C
2.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 0 - 20 °C
3.1: ammonium hydroxide / 1,4-dioxane; water / 120 - 125 °C / autoclave
4.1: bromine / dichloromethane / 0 - 5 °C
4.2: 0 - 5 °C / pH 9 - 10
View Scheme
4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water; acetone / 3 - 30 °C
1.2: 0.17 h / 10 °C / Inert atmosphere
1.3: 2 h / 10 °C
2.1: ammonia / 1-methyl-pyrrolidin-2-one; water / 19 h / 120 °C
3.1: bromine / propan-1-ol / 5 - 20 °C
3.2: 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 2 h / 0 - 5 °C / Large scale reaction
2: ammonia / 1,4-dioxane; water / 12 h / 120 °C / Autoclave; Large scale reaction
3: bromine / dichloromethane / 4 h / 0 - 5 °C
View Scheme
Multi-step reaction with 6 steps
1.1: nitric acid / ethanol; water / 16 h / Reflux
2.1: ethanol; sodium / 12 h / Reflux
3.1: trichlorophosphate; N,N-dimethyl-aniline / 6 h / Reflux
4.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 45 °C
5.1: ammonia / 1,4-dioxane; water / 12 h / 120 °C
6.1: bromine / dichloromethane / 4 h / 0 - 5 °C
6.2: pH 9 - 10
View Scheme
4-((2,6-dichloropyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile
1225383-63-0

4-((2,6-dichloropyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 2 h / 0 - 5 °C / Large scale reaction
2: ammonia / 1,4-dioxane; water / 12 h / 120 °C / Autoclave; Large scale reaction
3: bromine / dichloromethane / 4 h / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 0 - 20 °C
2.1: ammonium hydroxide / 1,4-dioxane; water / 120 - 125 °C / autoclave
3.1: bromine / dichloromethane / 0 - 5 °C
3.2: 0 - 5 °C / pH 9 - 10
View Scheme
Multi-step reaction with 3 steps
1: 1-methyl-pyrrolidin-2-one; potassium tert-butylate / 2.5 h / 0 - 5 °C
2: ammonia; 1-methyl-pyrrolidin-2-one / water / 0.5 h / 130 °C / 6723.1 Torr / Microwave irradiation
3: bromine / dichloromethane / 5 h / 0 - 5 °C
View Scheme
1-(4-cyanophenyl)guanidine
5637-42-3

1-(4-cyanophenyl)guanidine

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: ethanol; sodium / 12 h / Reflux
2.1: trichlorophosphate; N,N-dimethyl-aniline / 6 h / Reflux
3.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 45 °C
4.1: ammonia / 1,4-dioxane; water / 12 h / 120 °C
5.1: bromine / dichloromethane / 4 h / 0 - 5 °C
5.2: pH 9 - 10
View Scheme
Multi-step reaction with 6 steps
1.1: potassium tert-butylate / butan-1-ol / 4 h / 60 - 93 °C
2.1: trichlorophosphate / 20 - 85 °C
2.2: pH 9 - 10
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dmap / 1-methyl-pyrrolidin-2-one / 0.5 h
3.2: 4.5 h / 20 - 85 °C
4.1: N-Bromosuccinimide; ammonium acetate / dichloromethane / 4 h
4.2: pH 10 - 11
5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 1 h / 20 °C
5.2: 24.5 h / 100 - 110 °C
6.1: sodium hydroxide; water / isopropyl alcohol / 5.5 h / 20 - 75 °C
View Scheme
Multi-step reaction with 5 steps
1.1: sodium; ethanol / 12 h / Reflux
2.1: trichlorophosphate; N,N-dimethyl-aniline / 6 h / Reflux
3.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 45 °C
4.1: ammonium hydroxide / water; 1,4-dioxane / 12 h / 120 °C
5.1: bromine / dichloromethane / 4 h / 0 - 5 °C
5.2: pH 9-10
View Scheme
Multi-step reaction with 6 steps
1: potassium tert-butylate / butan-1-ol / 4 h / 45 - 93 °C
2: trichlorophosphate / 7 h / 27 - 97 °C
3: dmap / acetonitrile / 7 h / 27 - 78 °C
4: bromine; acetic acid / dichloromethane / 11 h / 27 °C
5: 1,8-diazabicyclo[5.4.0]undec-7-ene; dmap / N,N-dimethyl-formamide / 5 h / 27 - 73 °C
6: lithium hydroxide monohydrate / acetonitrile; isopropyl alcohol / 10 h / 27 - 59 °C
View Scheme
Multi-step reaction with 5 steps
1: sodium; methanol / methanol / 6 h / Reflux; Inert atmosphere
2: trichlorophosphate / 12 h / 90 - 95 °C
3: N-Bromosuccinimide / tetrahydrofuran / 20 °C
4: ammonia / 1,4-dioxane / 1 h / 50 °C / Sealed tube
5: potassium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 80 °C / Inert atmosphere
View Scheme
4-((4-amino-6-chloropyrimidin-2-yl)amino)benzonitrile
1398507-08-8

4-((4-amino-6-chloropyrimidin-2-yl)amino)benzonitrile

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dmap / 1-methyl-pyrrolidin-2-one / 0.5 h
1.2: 4.5 h / 20 - 85 °C
2.1: N-Bromosuccinimide; ammonium acetate / dichloromethane / 4 h
2.2: pH 10 - 11
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 1 h / 20 °C
3.2: 24.5 h / 100 - 110 °C
4.1: sodium hydroxide; water / isopropyl alcohol / 5.5 h / 20 - 75 °C
View Scheme
Multi-step reaction with 2 steps
1.1: bromine / methanol / 2.17 h / 0 - 5 °C
2.1: potassium carbonate; potassium iodide / 1-methyl-pyrrolidin-2-one / 0.17 h / 0 - 5 °C / Inert atmosphere
2.2: 26.5 h / 10 - 120 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: dmap / acetonitrile / 7 h / 27 - 78 °C
2: bromine; acetic acid / dichloromethane / 11 h / 27 °C
3: 1,8-diazabicyclo[5.4.0]undec-7-ene; dmap / N,N-dimethyl-formamide / 5 h / 27 - 73 °C
4: lithium hydroxide monohydrate / acetonitrile; isopropyl alcohol / 10 h / 27 - 59 °C
View Scheme
N-[6-chloro-2-(4-cyanophenylamino)pyrimidin-4-yl]benzamide
1404118-66-6

N-[6-chloro-2-(4-cyanophenylamino)pyrimidin-4-yl]benzamide

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-Bromosuccinimide; ammonium acetate / dichloromethane / 4 h
1.2: pH 10 - 11
2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 1 h / 20 °C
2.2: 24.5 h / 100 - 110 °C
3.1: sodium hydroxide; water / isopropyl alcohol / 5.5 h / 20 - 75 °C
View Scheme
Multi-step reaction with 3 steps
1: bromine; acetic acid / dichloromethane / 11 h / 27 °C
2: 1,8-diazabicyclo[5.4.0]undec-7-ene; dmap / N,N-dimethyl-formamide / 5 h / 27 - 73 °C
3: lithium hydroxide monohydrate / acetonitrile; isopropyl alcohol / 10 h / 27 - 59 °C
View Scheme
N-[5-bromo-6-(4-cyano-2,6-dimethylphenoxy)-2-(4-cyano-phenylamino)pyrimidin-4-yl]-benzamide
1404118-68-8

N-[5-bromo-6-(4-cyano-2,6-dimethylphenoxy)-2-(4-cyano-phenylamino)pyrimidin-4-yl]-benzamide

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
With water; sodium hydroxide In isopropyl alcohol at 20 - 75℃; for 5.5h; Product distribution / selectivity;
With lithium hydroxide monohydrate In isopropyl alcohol; acetonitrile at 27 - 59℃; for 10h; Solvent; Time; Temperature; Reagent/catalyst;75 mg
4-(4-amino-6-hydroxy-pyrimidin-2-ylamino)-benzonitrile
1398507-07-7

4-(4-amino-6-hydroxy-pyrimidin-2-ylamino)-benzonitrile

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: trichlorophosphate / 20 - 85 °C
1.2: pH 9 - 10
2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dmap / 1-methyl-pyrrolidin-2-one / 0.5 h
2.2: 4.5 h / 20 - 85 °C
3.1: N-Bromosuccinimide; ammonium acetate / dichloromethane / 4 h
3.2: pH 10 - 11
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 1 h / 20 °C
4.2: 24.5 h / 100 - 110 °C
5.1: sodium hydroxide; water / isopropyl alcohol / 5.5 h / 20 - 75 °C
View Scheme
Multi-step reaction with 5 steps
1: trichlorophosphate / 7 h / 27 - 97 °C
2: dmap / acetonitrile / 7 h / 27 - 78 °C
3: bromine; acetic acid / dichloromethane / 11 h / 27 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene; dmap / N,N-dimethyl-formamide / 5 h / 27 - 73 °C
5: lithium hydroxide monohydrate / acetonitrile; isopropyl alcohol / 10 h / 27 - 59 °C
View Scheme
5-bromo-2,6-dichloropyrimidin-4-amine
101012-11-7

5-bromo-2,6-dichloropyrimidin-4-amine

3,5-dimethyl-4-hydroxybenzonitrile
4198-90-7

3,5-dimethyl-4-hydroxybenzonitrile

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Stage #1: 5-bromo-2,6-dichloropyrimidin-4-amine With sodium hydride In ISOPROPYLAMIDE; mineral oil at 0 - 5℃; for 0.333333h; Inert atmosphere;
Stage #2: 3,5-dimethyl-4-hydroxybenzonitrile In ISOPROPYLAMIDE; mineral oil at 10 - 80℃; for 19.5h;
Stage #3: 4-Aminobenzonitrile
4-(6-amino-5-bromo-2-chloropyrimidin-4-yloxy)-3,5-dimethylbenzonitrile
1415796-11-0

4-(6-amino-5-bromo-2-chloropyrimidin-4-yloxy)-3,5-dimethylbenzonitrile

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
With zinc(II) chloride In 1,4-dioxane at 100℃; for 44h; Inert atmosphere;
4-(6-(acetylamino)-2-chloropyrimidin-4-yloxy)-3,5-dimethylbenzonitrile

4-(6-(acetylamino)-2-chloropyrimidin-4-yloxy)-3,5-dimethylbenzonitrile

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: zinc(II) chloride / 1,4-dioxane / 43 h / 90 - 100 °C
2: potassium hydroxide; water / ethanol / 20 °C
3: bromine / N,N-dimethyl-formamide / 1 h / -10 - -5 °C
View Scheme
4-(4-amino-6-chloropyrimidin-2-ylamino)benzonitrile hydrochloride

4-(4-amino-6-chloropyrimidin-2-ylamino)benzonitrile hydrochloride

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water; acetone / 3.08 h / 0 - 40 °C
2.1: bromine / methanol / 2.17 h / 0 - 5 °C
3.1: potassium carbonate; potassium iodide / 1-methyl-pyrrolidin-2-one / 0.17 h / 0 - 5 °C / Inert atmosphere
3.2: 26.5 h / 10 - 120 °C / Inert atmosphere
View Scheme
4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-2-pyrimidinyl]-amino]benzonitrile
269055-04-1

4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-2-pyrimidinyl]-amino]benzonitrile

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine; hydrogenchloride; dmap / tetrahydrofuran; water / 1 h / 20 °C
2.1: silver(II) fluoride / acetonitrile / 2 h / 20 °C / Inert atmosphere; Glovebox; Sealed tube
3.1: ammonium hydroxide / isopropyl alcohol / 0.5 h / 80 °C / Inert atmosphere; Glovebox
3.2: 0.5 h / 20 °C / Inert atmosphere; Glovebox
View Scheme
C25H21BrFN5O3

C25H21BrFN5O3

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Stage #1: C25H21BrFN5O3 With ammonium hydroxide In isopropyl alcohol at 80℃; for 0.5h; Inert atmosphere; Glovebox;
Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20℃; for 0.5h; Inert atmosphere; Glovebox;
122 mg
4-(5-bromo-2-chloro-pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile
1039021-95-8

4-(5-bromo-2-chloro-pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile

etravirine
269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 0.42 h / 165 °C / Inert atmosphere; Glovebox; Sealed tube
2.1: N-ethyl-N,N-diisopropylamine; hydrogenchloride; dmap / tetrahydrofuran; water / 1 h / 20 °C
3.1: silver(II) fluoride / acetonitrile / 2 h / 20 °C / Inert atmosphere; Glovebox; Sealed tube
4.1: ammonium hydroxide / isopropyl alcohol / 0.5 h / 80 °C / Inert atmosphere; Glovebox
4.2: 0.5 h / 20 °C / Inert atmosphere; Glovebox
View Scheme
propargyl bromide
106-96-7

propargyl bromide

etravirine
269055-15-4

etravirine

4-((5-bromo-2-((4-cyanophenyl)amino)-6-(prop-2-yn-1-ylamino)pyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile

4-((5-bromo-2-((4-cyanophenyl)amino)-6-(prop-2-yn-1-ylamino)pyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h;63%
etravirine
269055-15-4

etravirine

C20H15BrN6O2

C20H15BrN6O2

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 0.5h; Heating / reflux;33%
etravirine
269055-15-4

etravirine

4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile hydrobromide
1030633-38-5

4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile hydrobromide

Conditions
ConditionsYield
With hydrogen bromide In dichloromethane; water
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

etravirine
269055-15-4

etravirine

etravirine tosylatee salt
1030633-41-0

etravirine tosylatee salt

Conditions
ConditionsYield
In acetone at 20℃; for 1h;
In nitromethane; ethanol
etravirine
269055-15-4

etravirine

etravirine phosphate
1253183-22-0

etravirine phosphate

Conditions
ConditionsYield
With phosphoric acid In water; acetone at 20℃; for 0.5h;
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