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CAS No.: | 733039-20-8 |
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Name: | 5-broMo-2-chloro-N-cyclopentylpyriMidin-4-aMine |
Article Data: | 31 |
Molecular Structure: | |
Formula: | C9H11BrClN3 |
Molecular Weight: | 276.563 |
Synonyms: | 5-broMo-2-chloro-N-cyclopentylpyriMidin-4-aMine;4-PyriMidinaMine, 5-broMo-2-chloro-N-cyclopentyl-;5-Bromo-2-chloro-4-(cyclopentylamino)pyrimidine;N-(5-Bromo-2-chloropyrimidin-4-yl)(cyclopentyl)amine |
EINECS: | 200-258-5 |
Density: | 1.643g/cm3 |
Boiling Point: | 424°C at 760 mmHg |
Flash Point: | 210.2°C |
Hazard Symbols: | T |
Risk Codes: | 25 |
Safety: | 45 |
PSA: | 37.81000 |
LogP: | 3.32000 |
Conditions | Yield |
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In 1,4-dioxane at 20℃; for 6h; | 100% |
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20℃; for 6h; Inert atmosphere; | 100% |
With sodium hydrogencarbonate In dichloromethane at 20℃; for 13h; Reagent/catalyst; Solvent; | 97.5% |
cyclopentyl chloride
4-amino-5-bromo-2-chloropyrimidine
5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine
Conditions | Yield |
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With triethylamine In methanol at 20℃; | 92.74% |
With copper diacetate; sodium hydroxide In dichloromethane at 80℃; for 10h; | 77% |
Cyclopentyl bromide
4-amino-5-bromo-2-chloropyrimidine
5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine
Conditions | Yield |
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With copper(II) trifluoroacetate; sodium hydroxide In 1,4-dioxane at 80℃; for 6h; Reagent/catalyst; Solvent; Temperature; | 90% |
2,4-dichloro-5-bromopyrimidine
Cyclopentamine
A
5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine
Conditions | Yield |
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With tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 20℃; Reagent/catalyst; |
2-butenoic acid
5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine
2-chloro-5-methyl-8-cyclopentylpyridin[2,3-d]pyrimidin-8-hydro-7-one
Conditions | Yield |
---|---|
With triethylamine; palladium dichloride In 1-methyl-pyrrolidin-2-one at 20 - 75℃; for 6h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere; | 94.8% |
Stage #1: 5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine With triethylamine; palladium dichloride In tetrahydrofuran at 60℃; for 5h; Stage #2: 2-butenoic acid In tetrahydrofuran for 2h; Temperature; Reagent/catalyst; Solvent; | 89.08% |
Stage #1: 2-butenoic acid; 5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine With bis(benzonitrile)palladium(II) dichloride; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine In tetrahydrofuran at 75℃; for 20h; Heck Reaction; Inert atmosphere; Stage #2: In acetic anhydride at 75℃; for 2h; Temperature; Reagent/catalyst; Solvent; | 80% |
With triethylamine; palladium dichloride In 1-methyl-pyrrolidin-2-one at 75℃; for 6h; Temperature; Inert atmosphere; |
tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate
5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine
tert-butyl 4-(6-{[5-bromo-4-(cyclopentylamino)pyrimidin-2-yl]amino}pyridin-3-yl)piperazine-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: 5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine With potassium carbonate In dichloromethane at 60℃; for 0.5h; Stage #2: tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate In dichloromethane at 20 - 60℃; for 1h; | 85% |
Stage #1: tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate; 5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine In xylene; butan-1-ol at 100 - 140℃; Stage #2: With sodium hydroxide In water; ethyl acetate; xylene; butan-1-ol |
5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine
prop-1-yne
Conditions | Yield |
---|---|
With triphenylphosphine; palladium dichloride In N,N-dimethyl-formamide at 50℃; for 20h; Reagent/catalyst; Solvent; Temperature; | 85% |
5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine
methyl iodide
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 1.5h; | 84% |
5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine
(E)-but-2-enoic acid
2-chloro-5-methyl-8-cyclopentylpyridin[2,3-d]pyrimidin-8-hydro-7-one
Conditions | Yield |
---|---|
Stage #1: 5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine; (E)-but-2-enoic acid With palladium diacetate; triethylamine In 1-methyl-pyrrolidin-2-one at 65℃; Inert atmosphere; Stage #2: With acetic anhydride In 1-methyl-pyrrolidin-2-one at 65℃; Inert atmosphere; | 81% |
Stage #1: 5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine; (E)-but-2-enoic acid With N-ethyl-N,N-diisopropylamine; palladium(II) chloride benzonitrile complex; tris-(o-tolyl)phosphine In tetrahydrofuran at 70℃; for 16h; Stage #2: With acetic anhydride In tetrahydrofuran for 1.5h; | 68% |
5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine
propargyl alcohol
3-(2-chloro-4-(cyclopentylamino)pyrimidin-5-yl)prop-2-yn-1-ol
Conditions | Yield |
---|---|
Stage #1: 5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine With copper(l) iodide; palladium on activated charcoal; N-ethyl-N,N-diisopropylamine; bis[2-(diphenylphosphino)phenyl] ether In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: propargyl alcohol In tetrahydrofuran for 5.5h; Reflux; Stage #3: With bis[2-(diphenylphosphino)phenyl] ether for 4h; Reflux; | 74.5% |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N-butylamine In tetrahydrofuran at 29℃; for 20h; Sonogashira Cross-Coupling; Inert atmosphere; Reflux; | 62% |
Stage #1: 5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine; propargyl alcohol With tetrabutyl ammonium fluoride; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; water at 25 - 67℃; for 2h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In ethyl acetate | 47.4% |