1. made in GMP plant, commerially 2. Normal Stock: 500kgs 3. Audit accepted. Related documents are available to offer and audited by many clients, such as Lupin, MSN, Dr reddy etc 4. Chromatographic Purity (HPLC): not less than 99.0% 5. Chi
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inquiryShandong Mopai Biotechnology 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 chemicals. W
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inquiryQuality assurance, stable process and affordable priceAppearance:detailed see specifications Storage:enquiry Package:according to the clients requirement Application:Pharmaceutical intermediates Transportation:Normal Port:chengdu
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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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inquiryProduct Description Product Name 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine CAS No. 330786-24-8 Appearance White powder Assay ≥99% Capacity 20mt/year
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inquiryGood quality 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine CAS 330786-24-8 with factory price Company profile Wuhan Fortuna Chemical Co.,Ltd established in 2006, is a big integrative chemical enterprise being engaged in Pharmaceutical
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inquiry3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine CAS No.:330786-24-8 Name: 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine Molecular Structure Molecular Formula: C17H13N5O
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inquiryCangzhou Enke Pharma Tech Co.,ltd. is located in Cangzhou City, Hebei province ,where is a famous petroleum chemical industry city in China. Enke Pharma a high-tech enterprise ,and we are dedicated to developing and manufacturing new ap
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inquiry5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyriMidin-4-ylaMine Basic information Product Name: 5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyriMidin-4-ylaMine Synonyms: 5-(4-phenoxyphenyl)-7H-pyrrolo
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inquiryHanways Chempharm Co., Limited, the former is Hubei Hanways Pharchem CO.,Limited, set up in 2009 in Wuhan, China. We specialize in sourcing and supplying APIs, pharmaceutical intermediates, and fine chemicals for worldwide markets. The founder has d
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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
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inquiryProduct name: 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine Other name : Ibrutinib intermediate Cas no. : 330786-24-8 Specification : In-house Purity: 98% Stock: Fresh Application:330786-24-8
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inquiryA substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc
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inquiryformamide
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
at 150℃; for 8h; | 90% |
at 160 - 180℃; for 6h; | 51% |
at 180℃; for 4h; |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With ammonia In methanol for 12h; Reflux; | 89.2% |
formamide
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
Stage #1: 5-amino-3-(4-phenoxy)phenyl-4-cyano-2,3-dihydropyrazole; formamide With formic acid at 115 - 120℃; for 4h; Stage #2: With dihydrogen peroxide at 45 - 50℃; for 3h; Temperature; | 88.5% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol at 20℃; for 1h; Solvent; | 87.3% |
With triethylamine; hydrazine In tetrahydrofuran; 2-methyltetrahydrofuran at 95℃; for 2h; |
4-Phenoxybenzoic acid
4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; copper (I) acetate; caesium carbonate In dimethyl sulfoxide at 140℃; for 10h; Inert atmosphere; | 83.7% |
4-phenoxyiodobenzene
4-Aminopyrazolo<3,4-d>pyrimidin
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With potassium tert-butylate In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; | 82% |
4-Phenoxybenzoic acid
3-bromo-4-aminopyrazolo<3,4-d>pyrimidine
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; sodium carbonate; copper(I) bromide In N,N-dimethyl acetamide at 150℃; for 24h; Inert atmosphere; | 81.5% |
formamidine acetic acid
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
In toluene for 4h; Reflux; | 80% |
4-phenoxyphenylboronic acid
4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 180℃; for 0.166667h; Suzuki Coupling; Microwave irradiation; Inert atmosphere; | 79% |
With tetrakis(triphenylphosphine) palladium(0); potassium phosphate monohydrate In 1,4-dioxane; water for 24h; Inert atmosphere; Reflux; | 77% |
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 120℃; for 24h; Inert atmosphere; | 75% |
4-phenoxyphenylboronic acid
3-bromo-4-aminopyrazolo<3,4-d>pyrimidine
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 135℃; for 30h; Inert atmosphere; | 78.8% |
With tetrakis(triphenylphosphine) palladium(0); potassium phosphate tribasic trihydrate In 1,4-dioxane; water at 135℃; Inert atmosphere; | 78.8% |
5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile
formamide
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
at 180℃; for 4h; Suzuki Coupling; | 66% |
With acetic acid; N,N-dimethyl-formamide dimethyl acetal at 120℃; | |
at 135 - 140℃; Temperature; | 70 g |
3-chloro-4-amino-1H-pyrazolo[3,4-d]pyrimidine
4-Phenoxybenzoic acid
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With pyridine; potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 150℃; for 12h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere; | 64.1% |
4-Phenoxybenzoic acid
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With copper(l) iodide; bathophenanthroline; potassium tert-butylate In 5,5-dimethyl-1,3-cyclohexadiene for 48h; Inert atmosphere; Reflux; | 61.1% |
4-phenoxyphenylboronic acid
4-Aminopyrazolo<3,4-d>pyrimidin
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In water; N,N-dimethyl-formamide at 120℃; Inert atmosphere; | 40% |
phenyl 4-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)]phenyl ether
4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; N,N-dimethyl-formamide at 120℃; for 12h; Inert atmosphere; | 37% |
1-tert-butyl-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With hydrogenchloride; formic acid; water for 0.5h; Heating / reflux; |
4-Aminopyrazolo<3,4-d>pyrimidin
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-iodo-succinimide / N,N-dimethyl-formamide / 80 °C / Inert atmosphere 2: potassium phosphate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation; Sealed tube View Scheme | |
Multi-step reaction with 2 steps 1: N-iodo-succinimide / N,N-dimethyl-formamide / 2 h / 80 °C 2: potassium phosphate monohydrate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 24 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 2 steps 1: N-iodo-succinimide / N,N-dimethyl-formamide / 24 h / 75 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 60 h / 90 °C View Scheme |
4-Phenoxybenzoic acid
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: thionyl chloride / 1 h / Reflux 1.2: -10 - 20 °C 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran; acetonitrile; methanol / 48 h / 0 - 20 °C / Inert atmosphere 3.1: hydrazine hydrate / ethanol / 1 h 4.1: 4 h / 180 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1.1: thionyl chloride / toluene / 1 h / Reflux 1.2: 0 - 20 °C 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile; methanol / 48 h / 0 - 20 °C / Inert atmosphere 3.1: hydrazine hydrate / ethanol; water / 1 h / Heating 4.1: 4 h / 180 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1: thionyl chloride / 1 h / Reflux 2: N-ethyl-N,N-diisopropylamine / toluene; tetrahydrofuran / -10 - 20 °C 3: N-ethyl-N,N-diisopropylamine / tetrahydrofuran; acetonitrile; methanol / 48 h / 0 - 20 °C / Inert atmosphere 4: hydrazine hydrate / ethanol / 1 h / Heating 5: 4 h / 180 °C / Inert atmosphere View Scheme |
2-[hydroxy-(4-phenoxy-phenyl)-methylene]-malononitrile
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran; acetonitrile; methanol / 48 h / 0 - 20 °C / Inert atmosphere 2: hydrazine hydrate / ethanol / 1 h 3: 4 h / 180 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile; methanol / 48 h / 0 - 20 °C / Inert atmosphere 2: hydrazine hydrate / ethanol; water / 1 h / Heating 3: 4 h / 180 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran; acetonitrile; methanol / 48 h / 0 - 20 °C / Inert atmosphere 2: hydrazine hydrate / ethanol / 1 h / Heating 3: 4 h / 180 °C / Inert atmosphere View Scheme |
2-[(4-phenoxy-phenyl)-methoxy-methylene]-malononitrile
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol / 1 h 2: 4 h / 180 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol; water / 1 h / Heating 2: 4 h / 180 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol / 1 h / Heating 2: 4 h / 180 °C / Inert atmosphere View Scheme |
4-phenoxybenzoyl chloride
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / toluene; tetrahydrofuran / -10 - 20 °C 2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran; acetonitrile; methanol / 48 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate / ethanol / 1 h / Heating 4: 4 h / 180 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1: sodium hydride / 2-methyltetrahydrofuran / 0.5 h 2: sodium hydrogencarbonate / 1,4-dioxane / 70 °C 3: hydrazine hydrochloride; triethylamine / ethanol / 85 °C 4: N,N-dimethyl-formamide dimethyl acetal; acetic acid / 120 °C View Scheme | |
Multi-step reaction with 4 steps 1: sodium hydroxide / acetone; water / 2 h / 10 - 30 °C 2: sodium hydrogencarbonate / water; 1,4-dioxane / 2 h / Reflux 3: hydrazine hydrate / ethanol / 1 h / Reflux 4: 8 h / 150 °C View Scheme |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hypochlorite solution; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / water; dichloromethane / 1 h 2: N-ethyl-N,N-diisopropylamine; hydrazine hydrate / tetrahydrofuran / 4 h / 0 - 25 °C / Inert atmosphere 3: ammonia / methanol / 12 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: manganese(IV) oxide / dichloromethane / 5 h 2: ammonia / ethanol / 5 h / 0 °C 3: hydrazine hydrate / ethanol / 1 h / 20 °C View Scheme |
4-Bromodiphenyl ether
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: iodine; magnesium / tetrahydrofuran / 1 h / Inert atmosphere; Reflux 1.2: 1 h / -80 - 25 °C / Inert atmosphere 2.1: sodium hypochlorite solution; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / water; dichloromethane / 1 h 3.1: N-ethyl-N,N-diisopropylamine; hydrazine hydrate / tetrahydrofuran / 4 h / 0 - 25 °C / Inert atmosphere 4.1: ammonia / methanol / 12 h / Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -20 °C 1.2: 1 h / 0 °C 2.1: manganese(IV) oxide / dichloromethane / 5 h 3.1: ammonia / ethanol / 5 h / 0 °C 4.1: hydrazine hydrate / ethanol / 1 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: magnesium; iodine / tetrahydrofuran / 40 °C / Inert atmosphere 1.2: 0 - 25 °C 2.1: potassium hydroxide; palladium on activated charcoal / 1,4-dioxane / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 18 h / -78 - -40 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / N,N-dimethyl-formamide; water / 12 h / 120 °C / Inert atmosphere View Scheme |
2,6-dichloro-pyrimidine carbaldehyde
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: iodine; magnesium / tetrahydrofuran / 1 h / Inert atmosphere; Reflux 1.2: 1 h / -80 - 25 °C / Inert atmosphere 2.1: sodium hypochlorite solution; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / water; dichloromethane / 1 h 3.1: N-ethyl-N,N-diisopropylamine; hydrazine hydrate / tetrahydrofuran / 4 h / 0 - 25 °C / Inert atmosphere 4.1: ammonia / methanol / 12 h / Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -20 °C 1.2: 1 h / 0 °C 2.1: manganese(IV) oxide / dichloromethane / 5 h 3.1: ammonia / ethanol / 5 h / 0 °C 4.1: hydrazine hydrate / ethanol / 1 h / 20 °C View Scheme |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / diethyl ether / 0.5 h / 20 °C / Inert atmosphere 2: aluminum (III) chloride / dichloromethane / 50 °C / Inert atmosphere 3: ammonia / toluene / 60 °C / Schlenk technique; Inert atmosphere 4: triethylamine; hydrazine / 2-methyltetrahydrofuran; tetrahydrofuran / 2 h / 95 °C View Scheme |
4,6-dichloropyrimidine-5-carboxylic acid chloride
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aluminum (III) chloride / dichloromethane / 50 °C / Inert atmosphere 2: ammonia / toluene / 60 °C / Schlenk technique; Inert atmosphere 3: triethylamine; hydrazine / 2-methyltetrahydrofuran; tetrahydrofuran / 2 h / 95 °C View Scheme |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ammonia / ethanol / 5 h / 0 °C 2: hydrazine hydrate / ethanol / 1 h / 20 °C View Scheme |
Dichloro-methyl-(4-phenoxy-phenyl)-silane
4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With palladium on activated charcoal; potassium hydroxide In 1,4-dioxane Concentration; Reagent/catalyst; Inert atmosphere; Reflux; |
phenol
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4.17 h / 25 - 120 °C 1.2: 8.17 h / 0 - 30 °C 2.1: pivaloyl chloride; dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 8 h / 0 - 70 °C / Inert atmosphere 3.1: sodium carbonate / 1,4-dioxane / 5 h / 0 - 75 °C 4.1: hydrazine hydrate / methanol / 2 h / 25 - 30 °C 5.1: zinc(II) chloride / o-xylene / 20.17 h / 25 - 120 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 7 h / 100 °C 2.1: sodium hydroxide; water / ethanol / 1 h / 60 °C 3.1: thionyl chloride / dichloromethane / 11 h / 30 °C 4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 - 20 °C 4.2: 1 h / 0 °C 5.1: potassium carbonate / 1,4-dioxane / 2 h / 70 °C 6.1: hydrazine hydrate / ethanol / 1 h / 80 °C 7.1: 3 h / 170 °C / Inert atmosphere View Scheme |
4-fluorobenzaldehyde
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4.17 h / 25 - 120 °C 1.2: 8.17 h / 0 - 30 °C 2.1: pivaloyl chloride; dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 8 h / 0 - 70 °C / Inert atmosphere 3.1: sodium carbonate / 1,4-dioxane / 5 h / 0 - 75 °C 4.1: hydrazine hydrate / methanol / 2 h / 25 - 30 °C 5.1: zinc(II) chloride / o-xylene / 20.17 h / 25 - 120 °C View Scheme |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
4-fluorobenzaldehyde
4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo [3,4-d]pyrimidin-1-yl]benzaldehyde
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide | 92% |
With caesium carbonate In N,N-dimethyl-formamide | 92% |
With caesium carbonate In N,N-dimethyl-formamide | 92% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
diethyl (4-hydroxybutyl)phosphonate
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; | 92% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; | 92% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
ethylene dibromide
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; | 91% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
3-hydroxypyrrolidine
(R)-3-(4-phenoxyphenyl)-1-(pyrrolidin-3-yl)-1H-pyrazolo[3,4-d]-pyrimidin-4-amine
Conditions | Yield |
---|---|
Stage #1: 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine; 3-hydroxypyrrolidine With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20 - 50℃; | 89% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
(R)-3-(4-phenoxyphenyl)-1-(1-piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate In tetrahydrofuran at 35℃; Inert atmosphere; | 88.6% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate
(3R)‐4‐amino‐3‐(4-phenoxyphenyl)‐1‐(1‐tert-butoxycarbonylpiperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In ethyl acetate at 10 - 30℃; Solvent; Darkness; Industrial scale; | 88.1% |
Stage #1: tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 5℃; Mitsunobu Displacement; Inert atmosphere; Stage #2: 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine In tetrahydrofuran at 0 - 20℃; for 5h; Stage #3: With zinc(II) chloride In tetrahydrofuran at 30 - 40℃; for 2.5h; | 80.2% |
Stage #1: tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 5℃; for 0.166667h; Mitsunobu Displacement; Inert atmosphere; Stage #2: 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine In tetrahydrofuran at 0 - 20℃; for 5h; Mitsunobu Displacement; Inert atmosphere; | 72% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
N-tert-butoxycarbonyl-3-piperidinol
(R)-3-(4-phenoxyphenyl)-1-(1-piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With diethylazodicarboxylate In 1,4-dioxane at 20℃; Inert atmosphere; | 85.3% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere; | 85% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate
(R)-3-(4-phenoxyphenyl)-1-(1-piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 25℃; Temperature; Mitsunobu Displacement; Inert atmosphere; Large scale; | 85% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 30℃; for 25h; Concentration; Temperature; | 80.45% |
Stage #1: 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine; tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 5h; Mitsunobu Displacement; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 5h; | 69% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
(S)-N-trifluoroacetyl-3-hydroxypiperidine
(R)-3-(4-phenoxyphenyl)-1-(1-piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
Stage #1: 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine; (S)-N-trifluoroacetyl-3-hydroxypiperidine With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20 - 30℃; for 4.5h; Mitsunobu Displacement; Inert atmosphere; Stage #2: With water; sodium hydroxide In methanol at 20 - 30℃; for 2h; Stage #3: With hydrogenchloride In methanol; water at 45 - 55℃; for 3h; | 84.8% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
2-(N-tert-butoxycarbonylamino)ethanol
tert-butyl (2-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)carbamate
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Mitsunobu Displacement; | 84.1% |
With di-isopropyl azodicarboxylate In tetrahydrofuran at 20℃; for 5h; | |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 5h; Mitsunobu Displacement; | |
With di-isopropyl azodicarboxylate In tetrahydrofuran at 20℃; for 5h; | |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 5h; |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
triphenylphosphine
tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: triphenylphosphine With di-isopropyl azodicarboxylate In tetrahydrofuran at 0 - 5℃; Mitsunobu Displacement; Inert atmosphere; Stage #2: 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine; tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate In tetrahydrofuran at 0 - 5℃; Reagent/catalyst; | 84% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Inert atmosphere; | 83.65% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
(E/Z)-2-buten-1-ol
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Inert atmosphere; | 82.74% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
(3R)‐4‐amino‐3‐(4-phenoxyphenyl)‐1‐(1‐tert-butoxycarbonylpiperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 12h; | 82% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
1-Bromo-2-bromomethyl-benzene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h; | 82% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
3-methoxycarbonylbenzyl bromide
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 8h; | 81.6% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
(R)-3-(4-phenoxyphenyl)-1-(1-piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With azodicarboxylic acid diphenyl ester In ethyl acetate at 50℃; Inert atmosphere; | 81.3% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
4-chlorobenzyl bromide
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h; | 81% |
(S)-3-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
(3R)‐4‐amino‐3‐(4-phenoxyphenyl)‐1‐(1‐tert-butoxycarbonylpiperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine
Conditions | Yield |
---|---|
Stage #1: 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine With potassium carbonate In N,N-dimethyl-formamide at 21 - 22℃; for 2h; Stage #2: (S)-3-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester In N,N-dimethyl-formamide at 80℃; for 14h; Concentration; | 80% |
With dmap; caesium carbonate In N,N-dimethyl-formamide at 90℃; for 8h; | 70% |
o-fluorobenzyl bromide
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h; | 80% |
3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Cyclopentanol
PCI-29732
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Inert atmosphere; | 79.62% |
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