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2.d (d)
(d) 4-Chloro-1-methylethylpyrazolo[3,4-d]pyrimidine By substituting the product of part (c) in the procedure of Example 1(d), 4-chloro-1-methylethylpyrazolo[3,4-d]pyrimidine, m.p. 47°-49°, is obtained.
4-((1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)oxy)-2-nitroaniline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
74.3%
With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;
General procedure: To the mixture of <strong>[610-81-1]4-amino-3-nitrophenol</strong> (1.0g, 6.4mmol) in DMF (50mL), Cs2CO3 (3.12g, 9.6mmol) was added under the protection of nitrogen. The reaction mixture was stirred at r. t. for 1.5-2h, and then compound 4 (6.4mmol) was added slowly. After stirring overnight, the reaction mixture was diluted with EtOAc (50mL), washed with water and brine, dried over Na2SO4 and concentrated to give compound 5 as an orange solid.
With caesium carbonate In N,N-dimethyl-formamide at 0℃;
4.1.2 General procedure A for the synthesis of compounds (4)
General procedure: A suspension of compound 3 (6.5mmol) and Cs2CO3 (13.0mol) in dry DMF (25mL) was stirred at 0°C for 30min, and then iodide alkane (7.8mmol) was added. After stirring overnight, the reaction mixture was extracted with EtOAc (60mL× 3), washed with water, dried over Na2SO4, and concentrated in vacuo to give compound 4.
5-((1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)oxy)-1-methyl-N-(4-(trifluoromethoxy)phenyl)-1H-benzo[d]imidazol-2-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 4 steps
1.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
2.1: trifluoroacetic anhydride / dichloromethane / 1 h / 0 °C
2.2: 16 h / 0 - 20 °C
3.1: hydrazine; platinum on carbon / ethanol / 3 h / 20 °C
4.1: acetonitrile / 18 h / 20 °C
4.2: 6 h / 120 °C
5-((1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)oxy)-1-methyl-N-(p-tolyl)-1H-benzo[d]imidazol-2-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 4 steps
1.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
2.1: trifluoroacetic anhydride / dichloromethane / 1 h / 0 °C
2.2: 16 h / 0 - 20 °C
3.1: hydrazine; platinum on carbon / ethanol / 3 h / 20 °C
4.1: acetonitrile / 18 h / 20 °C
4.2: 6 h / 120 °C
N-(4-chloro-3-(trifluoromethyl)phenyl)-5-((1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)oxy)-1-methyl-1H-benzo[d]imidazol-2-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 4 steps
1.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
2.1: trifluoroacetic anhydride / dichloromethane / 1 h / 0 °C
2.2: 16 h / 0 - 20 °C
3.1: hydrazine; platinum on carbon / ethanol / 3 h / 20 °C
4.1: acetonitrile / 18 h / 20 °C
4.2: 6 h / 120 °C
N-(4-bromophenyl)-5-((1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)oxy)-1-methyl-1H-benzo[d]imidazol-2-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 4 steps
1.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
2.1: trifluoroacetic anhydride / dichloromethane / 1 h / 0 °C
2.2: 16 h / 0 - 20 °C
3.1: hydrazine; platinum on carbon / ethanol / 3 h / 20 °C
4.1: acetonitrile / 18 h / 20 °C
4.2: 6 h / 120 °C
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