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330786-24-8

Basic Information
CAS No.: 330786-24-8
Name: 5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyriMidin-4-ylaMine
Molecular Structure:
Molecular Structure of 330786-24-8 (5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyriMidin-4-ylaMine)
Formula: C17H13N5O
Molecular Weight: 303.31802
Synonyms: 5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyriMidin-4-ylaMine;3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyriMidin-4-aMine;4-aMino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyriMidine;5-(4-Phenoxyphenyl)-7H-pyrrolo[2,3-d]pyriMidin-4-aMine;ibrutinib N-2;1H-Pyrazolo[3,4-d]pyriMidin-4-aMine, 3-(4-phenoxyphenyl)-;Ibrutinib intermeidate N-2;Ibrutinib INT1
EINECS: 810-090-0
Density: 1.380±0.06 g/cm3(Predicted)
Melting Point:
Boiling Point: 577.4±50.0 °C(Predicted)
Flash Point:
Solubility:
Appearance:
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 89.71000
LogP: 3.97560
Synthetic route

3-amino-5-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
at 150℃; for 8h;90%
at 160 - 180℃; for 6h;51%
at 180℃; for 4h;

C17H11ClN4O

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With ammonia In methanol for 12h; Reflux;89.2%

5-amino-3-(4-phenoxy)phenyl-4-cyano-2,3-dihydropyrazole

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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%

(4-amino-6-chloropyrimidin-5-yl)(4-phenoxyphenyl)methanone

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 20℃; for 1h; Solvent;87.3%
With triethylamine; hydrazine In tetrahydrofuran; 2-methyltetrahydrofuran at 95℃; for 2h;
2215-77-2

4-Phenoxybenzoic acid

151266-23-8

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With [2,2]bipyridinyl; copper (I) acetate; caesium carbonate In dimethyl sulfoxide at 140℃; for 10h; Inert atmosphere;83.7%
2974-94-9

4-phenoxyiodobenzene

2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;82%
2215-77-2

4-Phenoxybenzoic acid

83255-86-1

3-bromo-4-aminopyrazolo<3,4-d>pyrimidine

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With 1,10-Phenanthroline; sodium carbonate; copper(I) bromide In N,N-dimethyl acetamide at 150℃; for 24h; Inert atmosphere;81.5%

3-amino-5-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile

3473-63-0

formamidine acetic acid

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
In toluene for 4h; Reflux;80%
51067-38-0

4-phenoxyphenylboronic acid

151266-23-8

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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%
51067-38-0

4-phenoxyphenylboronic acid

83255-86-1

3-bromo-4-aminopyrazolo<3,4-d>pyrimidine

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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%
330792-70-6

5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
at 180℃; for 4h; Suzuki Coupling;66%
With acetic acid; N,N-dimethyl-formamide dimethyl acetal at 120℃;
at 135 - 140℃; Temperature;70 g
637338-78-4

3-chloro-4-amino-1H-pyrazolo[3,4-d]pyrimidine

2215-77-2

4-Phenoxybenzoic acid

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With pyridine; potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 150℃; for 12h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere;64.1%
2215-77-2

4-Phenoxybenzoic acid

3-methanesulfonyloxy-4-amino-1H-pyrazolo[3,4-d]pyrimidine

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With copper(l) iodide; bathophenanthroline; potassium tert-butylate In 5,5-dimethyl-1,3-cyclohexadiene for 48h; Inert atmosphere; Reflux;61.1%
51067-38-0

4-phenoxyphenylboronic acid

2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In water; N,N-dimethyl-formamide at 120℃; Inert atmosphere;40%
269410-26-6

phenyl 4-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)]phenyl ether

151266-23-8

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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%
500789-47-9

1-tert-butyl-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With hydrogenchloride; formic acid; water for 0.5h; Heating / reflux;
2380-63-4

4-Aminopyrazolo<3,4-d>pyrimidin

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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
2215-77-2

4-Phenoxybenzoic acid

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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
330792-68-2

2-[hydroxy-(4-phenoxy-phenyl)-methylene]-malononitrile

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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
330792-69-3

2-[(4-phenoxy-phenyl)-methoxy-methylene]-malononitrile

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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
1623-95-6

4-phenoxybenzoyl chloride

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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

(4,6-dichloropyrimidin-5-yl)(4-phenoxyphenyl)methanol

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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
101-55-3

4-Bromodiphenyl ether

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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
5305-40-8

2,6-dichloro-pyrimidine carbaldehyde

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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

4,6-dichloro-pyrimidine-5-carboxylic acid

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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
87600-97-3

4,6-dichloropyrimidine-5-carboxylic acid chloride

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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

(4,6-dichloropyrimidin-5-yl)(4-phenoxyphenyl)methanone

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonia / ethanol / 5 h / 0 °C
2: hydrazine hydrate / ethanol / 1 h / 20 °C
View Scheme
25268-16-0

Dichloro-methyl-(4-phenoxy-phenyl)-silane

151266-23-8

4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With palladium on activated charcoal; potassium hydroxide In 1,4-dioxane Concentration; Reagent/catalyst; Inert atmosphere; Reflux;
108-95-2

phenol

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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
459-57-4

4-fluorobenzaldehyde

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

459-57-4

4-fluorobenzaldehyde

330794-01-9

4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo [3,4-d]pyrimidin-1-yl]benzaldehyde

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide92%
With caesium carbonate In N,N-dimethyl-formamide92%
With caesium carbonate In N,N-dimethyl-formamide92%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

63075-64-9

diethyl (4-hydroxybutyl)phosphonate

C25H30N5O4P

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃;92%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;92%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

106-93-4

ethylene dibromide

1-(2-bromoethyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;91%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

100243-39-8

3-hydroxypyrrolidine

1418272-84-0

(R)-3-(4-phenoxyphenyl)-1-(pyrrolidin-3-yl)-1H-pyrazolo[3,4-d]-pyrimidin-4-amine

Conditions
ConditionsYield
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%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

(S)-3-hydroxypiperidine-N-carboxylate methyl ester

1022150-12-4

(R)-3-(4-phenoxyphenyl)-1-(1-piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate In tetrahydrofuran at 35℃; Inert atmosphere;88.6%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

143900-44-1

tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate

1022150-11-3

(3R)‐4‐amino‐3‐(4-phenoxyphenyl)‐1‐(1‐tert-butoxycarbonylpiperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine

Conditions
ConditionsYield
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%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

85275-45-2

N-tert-butoxycarbonyl-3-piperidinol

1022150-12-4

(R)-3-(4-phenoxyphenyl)-1-(1-piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With diethylazodicarboxylate In 1,4-dioxane at 20℃; Inert atmosphere;85.3%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

C21H23NO7S

C31H28N6O5

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere;85%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

143900-44-1

tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate

1022150-12-4

(R)-3-(4-phenoxyphenyl)-1-(1-piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

1126736-20-6

(S)-N-trifluoroacetyl-3-hydroxypiperidine

1022150-12-4

(R)-3-(4-phenoxyphenyl)-1-(1-piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
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%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

26690-80-2

2-(N-tert-butoxycarbonylamino)ethanol

1414357-83-7

tert-butyl (2-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)carbamate

Conditions
ConditionsYield
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;
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

603-35-0

triphenylphosphine

143900-44-1

tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate

C45H43N6O3P

Conditions
ConditionsYield
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%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

3-(4-hydroxyphenyl)-1-(piperidin-1-yl)prop-2-en-1-one

(S)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Inert atmosphere;83.65%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

6117-91-5

(E/Z)-2-buten-1-ol

C21H19N5O

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Inert atmosphere;82.74%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

t-butyl-3(S)-chloro-piperidine-1-carboxylate

1022150-11-3

(3R)‐4‐amino‐3‐(4-phenoxyphenyl)‐1‐(1‐tert-butoxycarbonylpiperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 12h;82%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

3433-80-5

1-Bromo-2-bromomethyl-benzene

1-(2-bromobenzyl)-3-(4-phenoxyphenyl)-4-amino-1H-pyrazolo[3,4-d]pyrimidine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h;82%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

1129-28-8

3-methoxycarbonylbenzyl bromide

C26H21N5O3

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 8h;81.6%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

(S)-3-hydroxypiperidine-N-carboxylate allyl ester

1022150-12-4

(R)-3-(4-phenoxyphenyl)-1-(1-piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With azodicarboxylic acid diphenyl ester In ethyl acetate at 50℃; Inert atmosphere;81.3%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

622-95-7

4-chlorobenzyl bromide

1-(4-chlorobenzyl)-3-(4-phenoxyphenyl)-4-amino-1H-pyrazolo[3,4-d]pyrimidine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h;81%
940890-90-4

(S)-3-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

1022150-11-3

(3R)‐4‐amino‐3‐(4-phenoxyphenyl)‐1‐(1‐tert-butoxycarbonylpiperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine

Conditions
ConditionsYield
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%
446-48-0

o-fluorobenzyl bromide

330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

1-(2-fluorobenzyl)-3-(4-phenoxyphenyl)-4-amino-1H-pyrazolo[3,4-d]pyrimidine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h;80%
330786-24-8

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

96-41-3

Cyclopentanol

330786-25-9

PCI-29732

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Inert atmosphere;79.62%
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     China (Mainland)  |  Contact Details

    Business Type:Lab/Research institutions

    Tel:+86-27-65522452

    Address:No. 388 Gaoxin Road(No. 2), East Lake Hi-tech Development Zone, Wuhan, Hubei Province, PRC

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     China (Mainland)  |  Contact Details

    Business Type:Trading Company

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    Address:Room 302, 47 Changping Street, Chaoyang District, Changchun, Jilin Province,China

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     China (Mainland)  |  Contact Details

    Business Type:Trading Company

    Tel:+8613397160123

    Address:13th Floor, Tower B, Century Plaza, Zhongnan Road, Wuchang District, Wuhan, China.

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    Our Advantages: 1.We have abundant professional production experience. 2.We have our own chemical factory. 3.Sample is free of charge. 4. Reasonable Price, Excellent Quality & Attentive Service 5. Prompt reply: we can reply you

    ShanLong Biotechnology Co., Ltd. is a high-tech enterprise specializing in high-tech and high value-added cosmetic raw materials, pharmaceutical intermediates, chemical customizati

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     China (Mainland)  |  Contact Details

    Business Type:Trading Company

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    Address:QiaoXiQu

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    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

    Shandong Hanjiang Chemical Co., Ltd. is located in Qilu Petrochemical Industrial Park, Zibo City, Shandong Province, involving pesticide, medicine, chemical industry, coating, dy

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     China (Mainland)  |  Contact Details

    Business Type:Lab/Research institutions

    Tel:18369939125

    Address:95A, Xingyuan East Road, Zhangdian District

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    Business Type:Trading Company

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    Changzhou Pesan Chemical Co., Ltd. is a dynamic and professional chemical company. Since its establishment, We provide raw materials and intermediates for the pharmaceutical industry and organic electronic materials. All of our staff have a chem

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     China (Mainland)  |  Contact Details

    Business Type:Other

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    Address:No.7-9,Guanghua St.,Zhonglou District,Changzhou,China

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    Henan CoreyChem Co., Ltd, based on the original Zhengzhou Cote Chemical Research Institute, be brave in absorbing highly educated talents & overseas returnees; actively responded to Zhengzhou City High-tech Zone Government’s Special Care

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     China (Mainland)  |  Contact Details

    Business Type:Lab/Research institutions

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    span lang="EN-US" style="font-size: 9.0pt;font-family:"Arial",sans-serif;color:#4D4D4D">As a leading manufacturer and supplier of chemicals in china, weckchem not only supply popular chemicals, but also weckchem’s r&d center off

    Hangzhou Weckchem Co.,Ltd, located in Hangzhou,China, is specialized in Green chemicals and Fine chemicals over 10 years. Our main products are used in Fuel oil, Water treatment an

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     China (Mainland)  |  Contact Details

    Business Type:Other

    Tel:86-15158040660

    Address:Xiaoshan district

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    Betterbiochem is specialized in APIs, pharmaceutical intermediates & fine chemicals. 1. The best quality, competitive price. 2. The best service before or after shipment. 3. Rich experience in export operation. 4. Rich experience in

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     China (Mainland)  |  Contact Details

    Business Type:Lab/Research institutions

    Tel:+86-18013506594

    Address:No. 8 Building, 18 nong, Xi Yingnan Road, Pudong, Shanghai,China

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    Zhengzhou Kingorgchem Chemical Technology Co., Ltd. was founded on the basis of Organophosphorus Chemistry Lab of Institute of Chemistry Henan Academy of Sciences in 2015. The

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     China (Mainland)  |  Contact Details

    Business Type:Lab/Research institutions

    Tel:+86-371-65511936

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    Hangzhou Jinlan Pharm-Drugs Technology Co.,Ltd is located in Hangzhou, Zhejiang Province. Neighboring Ningbo port, Shanghai port, Hangzhou Xiaoshan Int’l Airport and Shanghai Pudon

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     China (Mainland)  |  Contact Details

    Business Type:Other

    Tel:+86-571-85829053

    Address:Rm A606, Fuyi Center, jianqiao street, Jianggan Area

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    The company is a high-tech enterprise providing comprehensive customer service for pharmaceutical companies at home and abroad in accordance with international standards. Our business includes research, development, process optimization and product

    Prime Molecular Co., Ltd. is an advanced chemical intermediates manufacture with ?two R&D centers and two production sites in China, all well-equipped with dedicated and profession

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    China (Mainland)  |  Contact Details

    Business Type:Trading Company

    Tel:0852-95636137

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     China (Mainland)  |  Contact Details

    Business Type:Lab/Research institutions

    Tel:86-021-58380978

    Address:Building 87,Lane 669, Dong Jing Road Shanghai,P.R.China

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