(2-chloropyrimidin-5-yl)boronic acid
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With N-chloro-succinimide; copper(l) chloride In acetonitrile at 80℃; for 16h; | 75% |
5-chloropyrimidin-2-amine
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite |
5-chloropyrimidin-2-one
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With trichlorophosphate |
2-hydroxypyrimidine hydrochloride
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With chlorine; N,N-dimethyl-aniline; trichlorophosphate Yield given. Multistep reaction; |
2-hydroxy-5-chloropyrimidine
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-hydroxypyrimidine With N,N-dimethyl-aniline; trichlorophosphate at 120℃; for 1h; Stage #2: With water at 0℃; | |
Stage #1: 5-chloro-2-hydroxypyrimidine With N,N-dimethyl-aniline; trichlorophosphate at 120℃; for 1h; Stage #2: With water | |
With trichlorophosphate In N,N-dimethyl-aniline at 120℃; for 1h; Inert atmosphere; | 6 g |
2,4,5-trichloropyrimidine
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
Stage #1: 2,4,5-trichloropyrimidine With hydrogen; palladium 10% on activated carbon In methanol at 50℃; for 2h; Stage #2: With sodium hydrogencarbonate In methanol; water at 20℃; | |
With acetic acid; zinc In tetrahydrofuran at 20℃; for 2h; Heating; Reflux; | |
With acetic acid; zinc In tetrahydrofuran for 2h; Reflux; | |
Stage #1: 2,4,5-trichloropyrimidine With acetic acid; zinc In tetrahydrofuran for 2h; Reflux; Stage #2: With sodium hydrogencarbonate; sodium hydroxide In dichloromethane; water pH=10; | |
With acetic acid; zinc In tetrahydrofuran at 20℃; Reflux; |
2,5-dichloropyrimidine
(5-Chloro-pyrimidin-2-yl)-cyano-acetic acid ethyl ester
Conditions | Yield |
---|---|
at 70℃; for 3h; | 100% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol Reflux; | 100% |
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With triethylamine In isopropyl alcohol at 80℃; for 3h; | 97% |
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; | 97% |
Conditions | Yield |
---|---|
With potassium phosphate; (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; copper(II) acetate monohydrate In water at 30℃; for 22h; Schlenk technique; Inert atmosphere; | 97% |
2,5-dichloropyrimidine
tri-n-butyl(vinyl)tin
2-chloro-4-vinylpyrimidine
Conditions | Yield |
---|---|
With 2-chloro-4-pyrimidine In 1,2-dichloro-ethane at 70℃; for 2h; | 94% |
2,5-dichloropyrimidine
sodium phenyl-methanolate
Conditions | Yield |
---|---|
In benzyl alcohol Ambient temperature; | 94% |
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With triethylamine In isopropyl alcohol at 120℃; for 3h; Microwave irradiation; | 93.1% |
N,N,N,N,N,N-hexamethylphosphoric triamide
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
Heating; | 92% |
2,5-dichloropyrimidine
1-butyn-4-ol
2-(but-3-ynyloxy)-5-chloropyrimidine
Conditions | Yield |
---|---|
Stage #1: 3-Butyn-1-ol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2,5-dichloropyrimidine In tetrahydrofuran at 20℃; for 17h; Inert atmosphere; | 92% |
Stage #1: 3-Butyn-1-ol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2,5-dichloropyrimidine In tetrahydrofuran at 20℃; for 17h; Inert atmosphere; | 92% |
Stage #1: 3-Butyn-1-ol With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: 2,5-dichloropyrimidine In tetrahydrofuran at 20℃; | 57% |
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; | 91% |
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 91% |
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h; | 90% |
Conditions | Yield |
---|---|
With NaOEt | 89% |
Conditions | Yield |
---|---|
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; 4-phenyl-N-methylpyridinium iodide; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc In dimethyl sulfoxide at 80℃; for 8h; Reagent/catalyst; Inert atmosphere; | 89% |
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 150℃; for 3h; Solvent; Microwave irradiation; | 88.2% |
With triethylamine In N,N-dimethyl acetamide at 150℃; for 3h; Microwave irradiation; | 88% |
2,5-dichloropyrimidine
1-propynyltributylstannane
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 80℃; | 88% |
2,5-dichloropyrimidine
4-((1r,4r)-4-(1-(5-chloropyrimidin-2-yl)piperidin-4-yloxy)cyclohexyloxy)nicotinonitrile
Conditions | Yield |
---|---|
With potassium carbonate In isopropyl alcohol at 100℃; for 4h; Microwave irradiation; | 87.7% |
morpholine
2,5-dichloropyrimidine
4-(5-chloropyrimidin-2-yl)morpholine
Conditions | Yield |
---|---|
With potassium phosphate; (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; copper(II) acetate monohydrate In water at 30℃; for 22h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 87% |
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With potassium phosphate In toluene at 110℃; for 3h; | 86% |
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; | 85% |
Conditions | Yield |
---|---|
Stage #1: 9-phenyl-3,3'-bicarbazole With sodium hydride In N,N-dimethyl-formamide for 0.5h; Stage #2: 2,5-dichloropyrimidine In N,N-dimethyl-formamide at 20℃; for 4h; | 84% |
4-piperidinemethanol
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With triethylamine In acetonitrile for 16h; Reflux; | 82.4% |
With triethylamine In acetonitrile for 16h; Reflux; | 82.4% |
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With potassium fluoride In dimethyl sulfoxide at 120℃; for 2h; | 82% |
3-(piperidin-4-yl)propan-1-ol
2,5-dichloropyrimidine
3-(1-(5-chloropyrimidin-2-yl)piperidin-4-yl)propan-1-ol
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 60℃; | 82% |
2,5-dichloropyrimidine
(R)-3-aminopyrrolidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 30℃; | 81% |
4-ethylpiperazine
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With sodium sulfide In toluene at 40℃; for 12h; | 80% |
Conditions | Yield |
---|---|
In methanol at 20℃; for 1h; Sealed tube; regioselective reaction; | 80% |
2,5-dichloropyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h; | 80% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane at 90℃; Suzuki coupling; | 79% |
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane at 90℃; | 79% |
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