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Cas:269055-15-4
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inquiryThe 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
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
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inquiry1. 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
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inquiryDayangChem 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
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inquiryOur 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
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
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Cas:269055-15-4
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inquiryHenan 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
Cas:269055-15-4
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inquiryWITH 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
Cas:269055-15-4
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inquiryOur 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
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inquiry1. 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
Cas:269055-15-4
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inquiryProduct 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
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
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
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inquiry1.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
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inquiryOur 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
Cas:269055-15-4
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inquiryEtravirine 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
Cas:269055-15-4
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inquiryHello, 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
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&
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inquiry4-[[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
Cas:269055-15-4
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inquiry1. 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
Cas:269055-15-4
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inquiryHenan 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
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
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inquiryOur 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-
Cas:269055-15-4
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inquiryPacking: 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
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Cas:269055-15-4
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inquiryJ&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
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
Cas:269055-15-4
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Cas:269055-15-4
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inquiryetravirine
Conditions | Yield |
---|---|
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
3,5-dimethyl-4-hydroxybenzonitrile
etravirine
Conditions | Yield |
---|---|
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
etravirine
Conditions | Yield |
---|---|
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
etravirine
Conditions | Yield |
---|---|
With ammonia In isopropyl alcohol | 41% |
In water | 40.5% |
In water | 40.5% |
With ammonia In 1,4-dioxane at 150℃; for 96h; Sealed tube; | 0.44 g |
4-((4,6-dichloropyrimidin-2-yl)amino)benzonitrile
etravirine
Conditions | Yield |
---|---|
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
etravirine
Conditions | Yield |
---|---|
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
etravirine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 45 percent / N-methylpyrrolidine / dioxane 2: 41 percent / NH3 / propan-2-ol View Scheme |
etravirine
Conditions | Yield |
---|---|
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
etravirine
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20℃; for 1.25h; |
A
4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile hydrobromide
B
etravirine
Conditions | Yield |
---|---|
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
etravirine
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20℃; for 0.5h; |
etravirine tosylatee salt
etravirine
Conditions | Yield |
---|---|
With sodium hydroxide In water at 0 - 20℃; for 1.75h; Product distribution / selectivity; |
3,5-dimethyl-4-hydroxybenzonitrile
etravirine
Conditions | Yield |
---|---|
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
etravirine
Conditions | Yield |
---|---|
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
etravirine
Conditions | Yield |
---|---|
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
etravirine
Conditions | Yield |
---|---|
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
etravirine
Conditions | Yield |
---|---|
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
etravirine
Conditions | Yield |
---|---|
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
etravirine
Conditions | Yield |
---|---|
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
etravirine
Conditions | Yield |
---|---|
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
3,5-dimethyl-4-hydroxybenzonitrile
4-Aminobenzonitrile
etravirine
Conditions | Yield |
---|---|
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
4-Aminobenzonitrile
etravirine
Conditions | Yield |
---|---|
With zinc(II) chloride In 1,4-dioxane at 100℃; for 44h; Inert atmosphere; |
etravirine
Conditions | Yield |
---|---|
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 |
etravirine
Conditions | Yield |
---|---|
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
etravirine
Conditions | Yield |
---|---|
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 |
etravirine
Conditions | Yield |
---|---|
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
etravirine
Conditions | Yield |
---|---|
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
etravirine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h; | 63% |
etravirine
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 0.5h; Heating / reflux; | 33% |
etravirine
4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile hydrobromide
Conditions | Yield |
---|---|
With hydrogen bromide In dichloromethane; water |
Conditions | Yield |
---|---|
In acetone at 20℃; for 1h; | |
In nitromethane; ethanol |
etravirine
etravirine phosphate
Conditions | Yield |
---|---|
With phosphoric acid In water; acetone at 20℃; for 0.5h; |
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