N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethyl acetate for 3h; | 100% |
With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; for 3h; Inert atmosphere; | 100% |
With hydrazine hydrate In N,N-dimethyl-formamide at 100℃; for 3h; Green chemistry; | 100% |
imatinib
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid at 20℃; Reflux; | 97% |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane for 8h; | 95% |
(E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one
(2-methyl-5-aminophenyl)guanidine
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
In butan-1-ol at 70℃; | 92% |
2-bromo-4-nitrotoluene
4-pyridin-3-ylpyrimidin-2-ylamine
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Stage #1: 2-bromo-4-nitrotoluene; 4-pyridin-3-ylpyrimidin-2-ylamine With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; for 24h; Buchwald-Hartwig Coupling; Inert atmosphere; Stage #2: With potassium tert-butylate; bis(pinacol)diborane In 1,4-dioxane; isopropyl alcohol at 110℃; for 4h; Inert atmosphere; chemoselective reaction; | 83% |
hydrazine hydrate
N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With iron(III) chloride; pyrographite In water at 80℃; for 6 - 8h; | 80% |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 1.5h; | 75% |
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With diphenyl phosphoryl azide; triethylamine In toluene at 100℃; for 12h; Curtius Rearrangement; Stage #2: With hydrogenchloride In water; toluene at 100℃; | 60% |
Multi-step reaction with 2 steps 1: diphenyl phosphoryl azide; triethylamine / toluene / 12 h / 100 °C 2: trifluoroacetic acid / dichloromethane / 8 h View Scheme |
N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
In hydrogenchloride | 46% |
methyl-3-pyridylketone
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: ethanol / Heating 2: NaOH / propan-2-ol / 24 h / Heating 3: 8.9 g / SnCl2; aq. HCl / 0.5 h View Scheme | |
Multi-step reaction with 2 steps 1: 92 percent / xylene / 140 °C 2: 92 percent / butan-1-ol / 70 °C View Scheme | |
Multi-step reaction with 3 steps 2: 41.3 percent / sodium hydroxide / propan-2-ol / 8 h / Heating 3: 60.9 percent / H2 / palladium on charcoal / tetrahydrofuran / 21 h / 750.06 Torr / Ambient temperature View Scheme |
3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaOH / propan-2-ol / 24 h / Heating 2: 8.9 g / SnCl2; aq. HCl / 0.5 h View Scheme | |
Multi-step reaction with 2 steps 1: 4-methyl-2-pentanone / 12 h / Reflux 2: hydrazine hydrate / palladium 10% on activated carbon / methanol / 8 h / 25 °C / Reflux; Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium ethanolate / ethanol / 6 h / 78 °C 1.2: 0.17 h / 78 °C 2.1: sodium hydroxide / water 2.2: 20 °C 3.1: sodium tungstate monohydrate; water; dihydrogen peroxide / acetone / 10 h / 40 °C 4.1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 80 °C 5.1: iron(III) chloride hexahydrate; hydrazine hydrate / methanol / 6 h / 78 °C View Scheme |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaOH / propan-2-ol / 24 h / Heating 2: 8.9 g / SnCl2; aq. HCl / 0.5 h View Scheme | |
Multi-step reaction with 2 steps 1: 41.3 percent / sodium hydroxide / propan-2-ol / 8 h / Heating 2: 60.9 percent / H2 / palladium on charcoal / tetrahydrofuran / 21 h / 750.06 Torr / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: NaOH / propan-2-ol / Heating 2: H2 / 5percent Pd-C / tetrahydrofuran / 750.06 Torr / Ambient temperature View Scheme |
2-methyl-5-nitroaniline
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: HNO3 / ethanol / Heating 2: NaOH / propan-2-ol / 24 h / Heating 3: 8.9 g / SnCl2; aq. HCl / 0.5 h View Scheme | |
Multi-step reaction with 3 steps 1: aq. HCl / butan-1-ol / 150 °C 2: H2 / Pd/C / butan-1-ol 3: 92 percent / butan-1-ol / 70 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: nitric acid / ethanol / 25 - 50 °C 1.2: 3 h / Reflux 2.1: sodium hydroxide / water 3.1: 4-methyl-2-pentanone / 12 h / Reflux 4.1: hydrazine hydrate / palladium 10% on activated carbon / methanol / 8 h / 25 °C / Reflux; Inert atmosphere View Scheme |
1-(2-methyl-5-nitrophenyl)guanidine
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H2 / Pd/C / butan-1-ol 2: 92 percent / butan-1-ol / 70 °C View Scheme | |
Multi-step reaction with 2 steps 1: 4-methyl-2-pentanone / 12 h / Reflux 2: hydrazine hydrate / palladium 10% on activated carbon / methanol / 8 h / 25 °C / Reflux; Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1.1: acetic acid / 2 h / 90 - 95 °C 1.2: 12 h / Reflux 2.1: hydrazine hydrate / palladium 10% on activated carbon / methanol / 8 h / 25 °C / Reflux; Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: butan-1-ol / 9 h / 120 °C / Large scale 2: hydrogen / methanol / 45 h / 3102.97 Torr View Scheme | |
Multi-step reaction with 2 steps 1: butan-1-ol / 9 h / 120 °C 2: hydrogen / methanol / 45 h / 25 °C / 3102.97 Torr View Scheme |
(E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 41.3 percent / sodium hydroxide / propan-2-ol / 8 h / Heating 2: 60.9 percent / H2 / palladium on charcoal / tetrahydrofuran / 21 h / 750.06 Torr / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: NaOH / propan-2-ol / Heating 2: H2 / 5percent Pd-C / tetrahydrofuran / 750.06 Torr / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: sodium hydroxide / butan-1-ol / 4 h / 120 °C / Reflux 2: copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 15 h / 120 °C / Inert atmosphere; Reflux 3: iron(III) chloride; hydrazine hydrate / methanol / 6 h / 80 °C / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: sodium hydroxide / butan-1-ol / 20 h / Reflux; Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere 3: palladium on carbon; hydrogen / methanol / 760.05 Torr View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium methylate / ethanol; methanol / 6 h / 78 °C / Inert atmosphere; Molecular sieve 1.2: 0.5 h / 20 °C 2.1: sodium tungstate; dihydrogen peroxide / acetone / 10 h / 40 °C 3.1: triethylamine / 2-methyltetrahydrofuran / 5 h / 20 °C / Inert atmosphere 4.1: 5%-palladium/activated carbon; hydrogen / ethanol / 8 h / 20 °C / 1520.1 Torr View Scheme |
palladium
N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
In ethyl acetate | |
In ethyl acetate |
6-chloro-N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidin-amine
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With hydrogen; triethylamine; 5%-palladium/activated carbon In ethanol at 20℃; under 3750.38 Torr; for 40h; Product distribution / selectivity; | |
With hydrogen; triethylamine; 5% Pd(II)/C(eggshell) In ethanol at 20℃; under 3750.38 Torr; for 40h; Autoclave; |
1-(5-amino-2-methylphenyl)-3-[3-oxo-3-(3-pyridinyl)-1-prop-1-enyl]guanidine
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With potassium hydroxide In butan-1-ol for 18h; Product distribution / selectivity; Heating / reflux; |
β-oxo-3-pyridinepropanal sodium salt
(2-methyl-5-aminophenyl)guanidine
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Stage #1: β-oxo-3-pyridinepropanal sodium salt; (2-methyl-5-aminophenyl)guanidine With acetic acid In butan-1-ol at 20℃; for 1h; Inert atmosphere; Stage #2: With potassium hydroxide In butan-1-ol for 18h; Reflux; Inert atmosphere; |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide / water 2: 4-methyl-2-pentanone / 12 h / Reflux 3: hydrazine hydrate / palladium 10% on activated carbon / methanol / 8 h / 25 °C / Reflux; Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water 2.1: acetic acid / 2 h / 90 - 95 °C 2.2: 12 h / Reflux 3.1: hydrazine hydrate / palladium 10% on activated carbon / methanol / 8 h / 25 °C / Reflux; Inert atmosphere View Scheme |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium tungstate monohydrate; water; dihydrogen peroxide / acetone / 10 h / 40 °C 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 80 °C 3: iron(III) chloride hexahydrate; hydrazine hydrate / methanol / 6 h / 78 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium tungstate monohydrate; water; dihydrogen peroxide / acetone / 10 h / 40 °C 2: potassium carbonate / N,N-dimethyl-formamide / 80 °C 3: iron(III) chloride hexahydrate; hydrazine hydrate / methanol / 6 h / 78 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium tungstate; dihydrogen peroxide / acetone / 10 h / 40 °C 2: triethylamine / 2-methyltetrahydrofuran / 5 h / 20 °C / Inert atmosphere 3: 5%-palladium/activated carbon; hydrogen / ethanol / 8 h / 20 °C / 1520.1 Torr View Scheme |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 80 °C 2: iron(III) chloride hexahydrate; hydrazine hydrate / methanol / 6 h / 78 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 2: iron(III) chloride hexahydrate; hydrazine hydrate / methanol / 6 h / 78 °C View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / 2-methyltetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2: 5%-palladium/activated carbon; hydrogen / ethanol / 8 h / 20 °C / 1520.1 Torr View Scheme |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium hydroxide / water 1.2: 20 °C 2.1: sodium tungstate monohydrate; water; dihydrogen peroxide / acetone / 10 h / 40 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 80 °C 4.1: iron(III) chloride hexahydrate; hydrazine hydrate / methanol / 6 h / 78 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydroxide / water 1.2: 20 °C 2.1: sodium tungstate monohydrate; water; dihydrogen peroxide / acetone / 10 h / 40 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 4.1: iron(III) chloride hexahydrate; hydrazine hydrate / methanol / 6 h / 78 °C View Scheme | |
Multi-step reaction with 4 steps 1: 0.5 h / 20 °C 2: sodium tungstate; dihydrogen peroxide / acetone / 10 h / 40 °C 3: triethylamine / 2-methyltetrahydrofuran / 5 h / 20 °C / Inert atmosphere 4: 5%-palladium/activated carbon; hydrogen / ethanol / 8 h / 20 °C / 1520.1 Torr View Scheme |
2-bromo-4-nitrotoluene
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 15 h / 120 °C / Inert atmosphere; Reflux 2: iron(III) chloride; hydrazine hydrate / methanol / 6 h / 80 °C / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 20 h / 20 - 100 °C / Inert atmosphere; Schlenk technique 2: hydrazine hydrate; iron(III) chloride; pyrographite / water / 80 °C / Inert atmosphere; Schlenk technique View Scheme | |
Multi-step reaction with 2 steps 1: copper(l) iodide; potassium iodide; potassium carbonate / 1,4-dioxane / Inert atmosphere; Reflux 2: ammonium formate; palladium 10% on activated carbon / methanol / 4 h / 30 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: copper(l) iodide; N,N`-dimethylethylenediamine / 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation 2: zinc; ammonium chloride / tetrahydrofuran / 0.17 h / 80 °C / Microwave irradiation View Scheme | |
Multi-step reaction with 2 steps 1: copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 24 h / 120 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / ethyl acetate / Inert atmosphere View Scheme |
4-pyridin-3-ylpyrimidin-2-ylamine
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 15 h / 120 °C / Inert atmosphere; Reflux 2: iron(III) chloride; hydrazine hydrate / methanol / 6 h / 80 °C / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: potassium tert-butylate / dimethyl sulfoxide / 12 h / 120 °C 2: tin(ll) chloride; hydrogenchloride / methanol / 10 h / 50 °C View Scheme | |
Multi-step reaction with 2 steps 1: copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 20 h / 20 - 100 °C / Inert atmosphere; Schlenk technique 2: hydrazine hydrate; iron(III) chloride; pyrographite / water / 80 °C / Inert atmosphere; Schlenk technique View Scheme |
3-pyridylboronic acid
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1-(2,6-diisopropylphenyl)-3-(2-oxo-2-(2,4,6-tri-tert-butylphenylamino)ethyl)-1H-imidazol-3-ium bromide; palladium diacetate; sodium hydroxide / dimethyl sulfoxide; water / 10 h / 100 °C 2: potassium tert-butylate / dimethyl sulfoxide / 12 h / 120 °C 3: tin(ll) chloride; hydrogenchloride / methanol / 10 h / 50 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran; water / 12 h / 85 °C / Inert atmosphere 2.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 100 °C / Inert atmosphere 3.1: sodium hydroxide; water / ethanol / 5 h / 100 °C 4.1: diphenyl phosphoryl azide; triethylamine / toluene / 12 h / 100 °C 4.2: 100 °C View Scheme | |
Multi-step reaction with 5 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran; water / 12 h / 85 °C / Inert atmosphere 2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 100 °C / Inert atmosphere 3: sodium hydroxide; water / ethanol / 5 h / 100 °C 4: diphenyl phosphoryl azide; triethylamine / toluene / 12 h / 100 °C 5: trifluoroacetic acid / dichloromethane / 8 h View Scheme |
1-methyl-4-nitrobenzene
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: bromine; iron / 1.5 h / 80 °C / Inert atmosphere; Schlenk technique 2: copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 20 h / 20 - 100 °C / Inert atmosphere; Schlenk technique 3: hydrazine hydrate; iron(III) chloride; pyrographite / water / 80 °C / Inert atmosphere; Schlenk technique View Scheme | |
Multi-step reaction with 3 steps 1: sulfuric acid; N-Bromosuccinimide / water 2: copper(l) iodide; potassium iodide; potassium carbonate / 1,4-dioxane / Inert atmosphere; Reflux 3: ammonium formate; palladium 10% on activated carbon / methanol / 4 h / 30 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: 4-pyridin-3-ylpyrimidin-2-ylamine; iron; bromine / 80 °C 2: copper(l) iodide; N,N`-dimethylethylenediamine / 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation 3: zinc; ammonium chloride / tetrahydrofuran / 0.17 h / 80 °C / Microwave irradiation View Scheme |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dimethyl sulfoxide / 0.17 h / Irradiation 2: hydrogenchloride; acetic acid / 20 °C / Reflux View Scheme |
N-(2-methyl-5-nitrophenyl)guanidinium hydrochloride
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / isopropyl alcohol / 24 h / Reflux 2: hydrogen; platinum(IV) oxide / tetrahydrofuran / 1.5 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / propan-1-ol / 24 h / Reflux 2: platinum(IV) oxide; hydrogen View Scheme |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
3-Iodobenzoic acid
Conditions | Yield |
---|---|
Stage #1: 3-Iodobenzoic acid With thionyl chloride; N,N-dimethyl-formamide In N,N-dimethyl-formamide at 20℃; for 17h; Stage #2: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2.5h; | 100% |
1,1,1,3,3,3-hexamethyl-disilazane
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride for 5h; Reflux; | 99.6% |
chloro-trimethyl-silane
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 2h; Solvent; | 99.6% |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
imatinib
Conditions | Yield |
---|---|
Stage #1: 4-((4-methylpiperazin-1-yl)methyl)benzoyl chloride dihydrochloride; 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine In water at 0℃; Stage #2: With sodium hydroxide In water at 50 - 55℃; pH=9 - 9.5; Product distribution / selectivity; | 99.26% |
With pyridine at 0 - 20℃; for 1h; Product distribution / selectivity; | 95% |
Stage #1: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With pyridine for 0.333333h; Autoclave; Stage #2: 4-((4-methylpiperazin-1-yl)methyl)benzoyl chloride dihydrochloride at 0 - 25℃; for 8h; | 92.7% |
trimethylsilyl bromide
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With triethylamine In 2-methyltetrahydrofuran at 0 - 20℃; | 99.2% |
p-(chloromethyl)benzoyl chloride
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
4-(chloromethyl)-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]-amino}phenyl)benzamide
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 0 - 20℃; for 4h; | 99% |
With triethylamine In tetrahydrofuran at 0℃; for 1h; Large scale; | 98.1% |
With triethylamine In tetrahydrofuran at 0℃; for 4h; | 97.4% |
p-(chloromethyl)benzoyl chloride
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
4-(сhloromethyl)-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide hydrochloride
Conditions | Yield |
---|---|
In 1,4-dioxane at 22 - 34℃; for 2.75h; | 99% |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
imatinib
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 40 - 50℃; for 6h; Time; | 97.8% |
benzoyl chloride
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
N-(4-methyl-3(4-(pyridine-3-yl)pyrimidin-2-ylamino)phenyl)benzamide
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 25℃; for 3h; | 97% |
With pyridine for 23h; Ambient temperature; | 18.3% |
phosphonic acid diethyl ester
4-dimethylamino-benzaldehyde
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With nickel(II) oxide In neat (no solvent) for 0.25h; Reagent/catalyst; Microwave irradiation; | 96.2% |
indole-2,3-dione
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
In toluene for 24h; Dean-Stark; Reflux; | 96% |
4-[(4-methylpiperazin-1-yl)methyl]bromobenzene
carbon monoxide
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
imatinib
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 50℃; under 760.051 Torr; for 36h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; | 95.8% |
4-hydroxy-benzaldehyde
phosphonic acid diethyl ester
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With nickel(II) oxide In neat (no solvent) for 0.266667h; Microwave irradiation; | 95.8% |
4-Diethylaminobenzaldehyde
phosphonic acid diethyl ester
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With nickel(II) oxide In neat (no solvent) for 0.266667h; Microwave irradiation; | 95.7% |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
N-(5-azido-2-methylphenyl)-4-(pyridine-3-yl)pyrimidin-2-amine
Conditions | Yield |
---|---|
Stage #1: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1.5h; Stage #2: With sodium azide In water at 0 - 5℃; for 3h; | 95% |
With fluorosulfonyl azide; potassium hydrogencarbonate In tert-butyl methyl ether; water; N,N-dimethyl-formamide at 20℃; for 0.0833333h; | 85% |
Stage #1: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With sulfuric acid; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium azide In water at 0 - 20℃; for 3h; | 81% |
Stage #1: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With hydrogenchloride; sodium nitrite In water at 0℃; for 1h; Stage #2: With sodium azide In water at 0℃; for 2h; | |
With hydrogenchloride; sodium azide; sodium nitrite In water at 0℃; for 3h; |
succinic acid anhydride
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
C20H19N5O3
Conditions | Yield |
---|---|
With dmap In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; | 95% |
ammonium thiocyanate
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Stage #1: ammonium thiocyanate With benzoyl chloride In acetone for 0.0833333h; Reflux; Stage #2: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine In acetone Reflux; | 95% |
3,4,5-trimethoxy-benzaldehyde
phosphonic acid diethyl ester
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With nickel(II) oxide In neat (no solvent) for 0.25h; Microwave irradiation; | 94.4% |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
3-chlorobenzoate
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 1h; | 94% |
2-[(tert-butoxy)carbonyl]-1 ,2,3,4-tetrahydroisoquinoline-7-carboxylic acid
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h; | 94% |
4-(N,N-Dimethylaminocarbonyl)benzoic acid
trifluoroacetic acid
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Stage #1: 4-(N,N-Dimethylaminocarbonyl)benzoic acid; 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 50℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: trifluoroacetic acid In water; acetonitrile | 94% |
4-chlorobenzaldehyde
phosphonic acid diethyl ester
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With nickel(II) oxide In neat (no solvent) for 0.283333h; Microwave irradiation; | 93.8% |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
3,5-dinitrobenoyl chloride
N-[4-methyl-3-(4-pyridin-3-ylpyrimidin-2-ylamino)phenyl]-3,5-dinitrobenzamide
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; | 93% |
3-nitro-benzaldehyde
phosphonic acid diethyl ester
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
Conditions | Yield |
---|---|
With nickel(II) oxide In neat (no solvent) for 0.3h; Microwave irradiation; | 92.6% |
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
imatinib
Conditions | Yield |
---|---|
Stage #1: 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid dihydrochloride With pyridine; thionyl chloride at 50 - 60℃; for 3h; Stage #2: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine at -10 - 0℃; for 1h; | 92.5% |
Stage #1: 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid dihydrochloride With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 50℃; for 2h; Stage #2: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine In N,N-dimethyl-formamide at 70℃; for 12h; | 91% |
Stage #1: 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid dihydrochloride With pyridine; thionyl chloride at 20 - 50℃; for 1 - 2h; Stage #2: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With pyridine at 0 - 25℃; for 1h; Product distribution / selectivity; | 90% |
4-nitro-3-(trifluoromethyl)benzoyl chloride
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
N-[4-methyl-3-(4-pyridin-3-ylpyrimidin-2-ylamino)phenyl]-4-nitro-3-trifluoromethylbenzamide
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; | 92% |
With pyridine In dichloromethane at 0℃; | |
With triethylamine In tetrahydrofuran at 0 - 20℃; for 26h; | |
With triethylamine In tetrahydrofuran |
The N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine, with the CAS registry number 152460-10-1,is also known as Oleylamine, ethoxylated. It belongs to the product categories of Aromatics Compounds;Aromatics;Bases & Related Reagents;Inhibitors;Nucleotides. This chemical's molecular formula is C16H15N5 and molecular weight is 277.3237. What's more,Its systematic name is N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine. It is a yellow solid which is a selective inhibitor of protein kinase c
Physical properties about N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine are:
(1)ACD/LogP:1.68±0.46; (2)# of Rule of 5 Violations:0; (3)ACD/LogD (pH 5.5):1.63; (4)ACD/LogD (pH 7.4):1.68; (5)ACD/BCF (pH 5.5):9.82; (6)ACD/BCF (pH 7.4):11.11; (7)ACD/KOC (pH 5.5): 172.25; (8)ACD/KOC (pH 7.4): 194.96; (9)#H bond acceptors:5; (10)#H bond donors:3; (11)#Freely Rotating Bonds:3; (12)Index of Refraction:1.688; (13)Molar Refractivity:83.6±0.3 cm3; (14)Molar Volume:219.0±3.0 cm3; (15)Polarizability:33.1±0.5 10-24cm3; (16)Surface Tension:64.2±3.0 dyne/cm; (17)Density:1.3±0.1 g/cm3; (18)Flash Point:278.8±32.9 °C; (19)Enthalpy of Vaporization:81.4±3.0 kJ/mol; (20)Boiling Point:537.3±60.0 °C at 760 mmHg; (21)Vapour Pressure:0.0±1.4 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES:Cc1ccc(cc1Nc2nccc(n2)c3cccnc3)N;
(2)Std. InChI:InChI=1S/C16H15N5/c1-11-4-5-13(17)9-15(11)21-16-19-8-6-14(20-16)12-3-2-7-18-10-12/h2-10H,17H2,1H3,(H,19,20,21);
(3)Std. InChIKey:QGAIPGVQJVGBIA-UHFFFAOYSA-N.
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