Conditions | Yield |
---|---|
With trichlorophosphate Chlorination; | 70% |
2-sulfanylpyrimidine
2-chloropyrimidine
Conditions | Yield |
---|---|
Stage #1: 2-sulfanylpyrimidine With trichloroisocyanuric acid; water; benzyltrimethylammonium chloride In acetonitrile at -30 - -25℃; for 0.5h; Stage #2: With isobutylamine In acetonitrile Further stages.; | 70% |
With hydrogenchloride; sodium hypochlorite In dichloromethane; water | |
With thionyl chloride; dihydrogen peroxide In water; acetonitrile at 25℃; |
(2-chloropyrimidin-5-yl)boronic acid
2-chloropyrimidine
Conditions | Yield |
---|---|
With 2-bromo-pyridine; tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene Reflux; | 65% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 24h; Heating; | A 30% B 50% |
triethylaluminum
5-Bromo-2-chloropyrimidine
A
2-chloropyrimidine
B
2-chloro-5-ethylpyrimidine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 24h; Heating; | A 30% B 42% |
2,6-Dichloropyrimidine
triethylaluminum
A
2-chloropyrimidine
B
2-chloro-4-ethylpyrimidine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 24h; Heating; | A 25% B 37% |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In water at -15 - 0℃; for 2.25h; | 34% |
With hydrogenchloride; sodium nitrite | |
With hydrogenchloride; zinc(II) chloride; sodium nitrite In dichloromethane; water | |
With hydrogenchloride; zinc(II) chloride; sodium nitrite In dichloromethane; water | |
With hydrogenchloride; copper dichloride; sodium nitrite In dichloromethane |
Conditions | Yield |
---|---|
With zinc | |
With potassium acetate; palladium diacetate; bis(pinacol)diborane; tricyclohexylphosphine In 1,4-dioxane at 110℃; for 0.166667h; Inert atmosphere; | |
With hydrogen In methanol; ethanol at 20℃; |
2-pyrimidinone hydrochloride
2-chloropyrimidine
Conditions | Yield |
---|---|
With phosphorus pentachloride; trichlorophosphate | |
With trichlorophosphate |
1-methyl-1H-pyrazole
chloroform
A
1H-pyrrole-2-carbonitrile
B
2-chloropyrimidine
C
5-chloronicotinonitrile
Conditions | Yield |
---|---|
at 550 - 555℃; Yield given. Title compound not separated from byproducts; | |
at 550 - 555℃; Title compound not separated from byproducts; |
1-benzylpyrazole
chloroform
A
2-chloropyrimidine
B
2-phenylpyrimidine
C
α-carboline
Conditions | Yield |
---|---|
at 550 - 555℃; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
at 550 - 555℃; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
at 550 - 555℃; Title compound not separated from byproducts; |
chloroform
1-(pyridin-4-ylmethyl)-1H-pyrazol-5-amine
A
NH-pyrazole
B
2-chloropyrimidine
Conditions | Yield |
---|---|
at 550 - 555℃; Title compound not separated from byproducts; | |
at 550 - 555℃; |
chloroform
1-(4-chlorobenzyl)pyrazole
A
NH-pyrazole
B
2-chloropyrimidine
D
2-(4-chlorophenyl)pyrimidine
Conditions | Yield |
---|---|
at 550 - 555℃; Title compound not separated from byproducts; |
1-(pyridin-4-ylmethyl)-1H-pyrazol-5-amine
A
NH-pyrazole
B
2-chloropyrimidine
Conditions | Yield |
---|---|
With chloroform at 550 - 555℃; Title compound not separated from byproducts; |
1-(4-chlorobenzyl)pyrazole
A
NH-pyrazole
B
2-chloropyrimidine
D
2-(4-chlorophenyl)pyrimidine
Conditions | Yield |
---|---|
With chloroform at 550 - 555℃; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With potassium carbonate In ethanol |
2-Amino-4,6-dichloropyrimidine
2-(4-Methoxyphenyl)ethanol
2-chloropyrimidine
Conditions | Yield |
---|---|
With NaH In tetrahydrofuran |
2-Amino-4,6-dichloropyrimidine
1-(2-Chloroethyl)-4-methoxybenzene
2-chloropyrimidine
Conditions | Yield |
---|---|
With Na2S In water; N,N-dimethyl-formamide |
Conditions | Yield |
---|---|
With sodium bicarbonate; trifluoroacetic acid In dichloromethane |
2-chloropyrimidine
Conditions | Yield |
---|---|
In chloroform-d1; water at 20℃; |
2-chloropyrimidine
1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
7,16-Di-pyrimidin-2-yl-1,4,10,13-tetraoxa-7,16-diaza-cyclooctadecane
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 100℃; under 6000480 Torr; for 96h; | 100% |
2-chloropyrimidine
allylmagnesium bromide
4-allyl-2-chloro-3,4-dihydropyrimidine
Conditions | Yield |
---|---|
In tetrahydrofuran for 0.25h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With NmN'''-(butane-1,4-diyl)bisguanidine for 16h; Heating; | 100% |
2-chloropyrimidine
tert.-butyl lithium
4-(tert-butyl)-2-chloropyrimidine
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In diethyl ether at -30 - 0℃; for 1h; | 100% |
With acetic acid; bunazosin In tetrahydrofuran at -78℃; for 3h; |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride; 2-aminopyrimidine-4,6-diol; copper(I) bromide at 145 - 150℃; for 24h; | 100% |
With potassium carbonate In dimethyl sulfoxide at 70℃; for 24h; Inert atmosphere; | 95% |
With 1-methyl-3-(2-pyridinyl)-3,4,5,6-tetrahydropyrimidin-3-ium hexafluorophosphate; potassium tert-butylate; palladium diacetate In 1,2-dimethoxyethane at 100℃; for 0.666667h; Buchwald-Hartwig Coupling; Microwave irradiation; | 93% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride; 2-aminopyrimidine-4,6-diol; copper(I) bromide at 145 - 150℃; for 24h; | 100% |
With copper(I) oxide; 1,10-Phenanthroline; tetrabutyl ammonium fluoride at 140 - 145℃; for 24h; | 98% |
Stage #1: 2-methylimidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: 2-chloropyrimidine In N,N-dimethyl-formamide; mineral oil at 130℃; | 89% |
With potassium phosphate; benzoin oxime; copper diacetate In dimethyl sulfoxide at 80℃; Inert atmosphere; | 80% |
With copper; caesium carbonate; methyl-alpha-D-glucopyranoside In water; dimethyl sulfoxide at 110℃; for 14h; Sealed tube; Green chemistry; | 80% |
2-chloropyrimidine
2-pivaloylaminophenyl boronic acid
2,2-dimethyl-N-(2-pyrimidin-2-yl-phenyl)-propionamide
Conditions | Yield |
---|---|
Stage #1: 2-chloropyrimidine; tetrakis(triphenylphosphine) palladium(0) In glyco dimethyl ether at 15 - 25℃; for 0.333333 - 0.5h; Stage #2: 2-pivaloylaminophenyl boronic acid With sodium carbonate In 1,2-dimethoxyethane; water at 78 - 83℃; for 3h; Heating / reflux; | 100% |
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 20 - 83℃; | |
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 0 - 83℃; for 4.33333 - 5.5h; Heating / reflux; | |
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 83℃; for 11h; |
Conditions | Yield |
---|---|
With potassium carbonate; hydrazine hydrate at 100℃; for 0.5h; | 99.8% |
With hydrazine In pyridine at 25℃; for 1.5h; | 95% |
With hydrazine hydrate In ethanol Reflux; | 87% |
Conditions | Yield |
---|---|
With potassium phosphate; bis(η3-allyl-μ-chloropalladium(II)); 1,2-bis(diphenylphosphino)-1'-(diisopropylphosphino)-3',4-di-tert-butyl ferrocene In toluene at 115℃; for 20h; Inert atmosphere; | 99% |
With copper; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 0.166667h; Ullmann ether synthesis; microwave irradiation; | 97% |
With 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate; copper(l) chloride In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; Ullmann coupling; Inert atmosphere; | 65% |
Conditions | Yield |
---|---|
With potassium carbonate In neat (no solvent) at 160℃; for 3h; Schlenk technique; Inert atmosphere; | 99% |
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 24.5h; | 97% |
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 120℃; for 40h; | 97% |
2-chloropyrimidine
para-methylphenylmagnesium bromide
2-p-tolyl-pyrimidine
Conditions | Yield |
---|---|
With N-heterocyclic carbene-based nickel(II) complex In tetrahydrofuran at 20℃; for 12h; Kumada reaction; | 99% |
With chloro(1,3-bis(pyridin-2-ylmethyl)imidazolylidene)nickel(II) hexafluorophosphate In tetrahydrofuran at 20℃; for 12h; Kumada-Corriu coupling reaction; Inert atmosphere; | 99% |
With C16H16Cl2CoN8(1+)*F6P(1-) In tetrahydrofuran at 20℃; for 2h; Kumada-Corriu cross-coupling; | 97% |
With (IPr)Ni(π-allyl)Cl In tetrahydrofuran at 20℃; for 24h; Kumada Cross-Coupling; Inert atmosphere; | 74% |
With [Ni(1-(1-ethyl-benzimidazol-2-ylmethyl)-3-mesitylimidazolin-2-ylidene)2][Cl]2; sodium acetate In tetrahydrofuran at 20℃; Kumada-Corriu coupling reaction; Inert atmosphere; |
Conditions | Yield |
---|---|
With C21H18N8Ni2O(2+)*2F6P(1-) In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20 - 80℃; Negishi coupling reaction; | 99% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane at 90℃; Suzuki coupling reaction; | 99% |
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane at 90℃; Suzuki coupling; | 93% |
Suzuki coupling; |
2-chloropyrimidine
propan-1-ol-3-amine
3-(pyrimidin-2-ylamino)propan-1-ol
Conditions | Yield |
---|---|
In ethanol for 18h; Reflux; Inert atmosphere; | 99% |
With triethylamine In butan-1-ol at 125℃; for 1h; Temperature; Inert atmosphere; Microwave irradiation; | 87% |
2-chloropyrimidine
tert-butyl 2-[(R)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylate
tert-butyl 2-[(R)-5-(pyrimidin-2-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylate
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water Suzuki Coupling; Inert atmosphere; Heating; | 99% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water at 100℃; for 18h; Suzuki Coupling; |
Conditions | Yield |
---|---|
Stage #1: 2-(Trimethylsilyl)ethanol With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: 2-chloropyrimidine In tetrahydrofuran at 25℃; for 24h; | 99% |
4,4-ethylenedioxycyclohexan-1-ol
2-chloropyrimidine
2-(1,4-dioxaspiro[4.5]decan-8-yloxy)pyrimidine
Conditions | Yield |
---|---|
Stage #1: 4,4-ethylenedioxycyclohexan-1-ol With 1H-imidazole; sodium hydride In N,N-dimethyl acetamide; mineral oil at 20℃; for 0.5h; Cooling with ice; Stage #2: 2-chloropyrimidine In N,N-dimethyl acetamide; mineral oil at 20 - 60℃; for 3.5h; | 98.59% |
Stage #1: 4,4-ethylenedioxycyclohexan-1-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: 2-chloropyrimidine In N,N-dimethyl-formamide; mineral oil at 0 - 70℃; for 17h; | 97% |
Stage #1: 4,4-ethylenedioxycyclohexan-1-ol With sodium hydride In N,N-dimethyl-formamide for 0.333333h; Stage #2: 2-chloropyrimidine at 20 - 100℃; for 9.5h; | |
Stage #1: 4,4-ethylenedioxycyclohexan-1-ol With sodium hydride In N,N-dimethyl-formamide for 0.333333h; Stage #2: 2-chloropyrimidine In N,N-dimethyl-formamide at 100℃; for 9h; |
Conditions | Yield |
---|---|
With cesium acetate; copper In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; | 98% |
at 100℃; for 0.1h; microwave irradiation; | 91% |
With triethylamine In ethanol at 120℃; for 0.0833333h; Microwave irradiation; | 89% |
2-chloropyrimidine
(2-propoxyphenyl)boronic acid
2-(2-Propoxyphenyl)pyrimidine
Conditions | Yield |
---|---|
<1,4-bis-(diphenylphosphine)butane>palladium(II) | 98% |
With sodium carbonate; [1,4-bis(diphenylphosphino)butane] palladium(ll) dichloride In ethanol; toluene for 24h; Heating; | 98% |
2-chloropyrimidine
2-Methylphenylboronic acid
2-(2-methylphenyl)pyrimidine
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane at 90℃; Suzuki coupling reaction; | 98% |
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane at 90℃; Suzuki coupling; | 93% |
With Tedicyp; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In xylene at 130℃; for 20h; Suzuki cross-coupling reaction; | 87% |
Suzuki coupling; |
2-chloropyrimidine
5-(pyrimidin-2-yl)-2,3-dihydro-1H-inden-1-one
Conditions | Yield |
---|---|
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; water at 20 - 95℃; Inert atmosphere; | 98% |
With sodium carbonate In 1,2-dimethoxyethane at 95℃; Suzuki Coupling; Inert atmosphere; | 41% |
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); 1,1',3,3'-tetrakis(diphenylphosphino)ferrocene; sodium t-butanolate In toluene for 17h; Catalytic behavior; Inert atmosphere; Schlenk technique; Heating; | 98% |
With fac-tris[2-phenylpyridinato-C2,N]iridium(III); caesium carbonate In N,N-dimethyl-formamide at 25℃; for 18h; Schlenk technique; Inert atmosphere; Irradiation; | 83% |
Stage #1: 2-chloropyrimidine With tris-(dibenzylideneacetone)dipalladium(0); triethylamine In toluene at 115℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: thiophenol In toluene at 115℃; for 24h; Reagent/catalyst; Time; Inert atmosphere; Schlenk technique; | 72% |
Conditions | Yield |
---|---|
With C50H61Cl2N3Pd; potassium tert-butylate In 1,4-dioxane at 100℃; for 2h; | 98% |
With C48H55ClN2Pd; sodium t-butanolate In 1,2-dimethoxyethane at 20℃; for 16h; Inert atmosphere; Sealed tube; | 98% |
With potassium carbonate In tetrahydrofuran for 2h; Reflux; | 44% |
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; zinc diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 16h; Buchwald-Hartwig Coupling; Inert atmosphere; | 98% |
2-chloropyrimidine
N,N-dimethyloctanamide
A
2-(dimethylamino)pyrimidine
B
Methyl-octyl-pyrimidin-2-yl-amine
Conditions | Yield |
---|---|
In tetrahydrofuran at 100℃; under 6000480 Torr; for 96h; | A 2% B 97% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane at 90℃; Suzuki coupling reaction; | 97% |
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane at 90℃; | 95% |
With oxygen; palladium diacetate; sodium carbonate In 1,4-dioxane at 90℃; Suzuki Coupling; | 93% |
2-chloropyrimidine
2-fluoropyrimidine
Conditions | Yield |
---|---|
With hydrogen fluoride at 50℃; for 1h; other aromatic halides, var. temp., also with HF-base systems; | 97% |
With hydrogen fluoride at 50℃; for 1h; | 97% |
2-chloropyrimidine
1-aza-18-crown-6
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 100℃; under 6000480 Torr; for 96h; | 97% |
Conditions | Yield |
---|---|
for 3h; Reflux; | 97% |
at 20℃; for 2h; | 95% |
for 2h; Heating; Yield given; |
Conditions | Yield |
---|---|
In N,N,N,N,N,N-hexamethylphosphoric triamide at 85℃; for 0.00833333h; microwave irradiation; | 97% |
In ethanol for 4h; Heating; | 14% |
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