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N,N-dimethyl-formamide
uridine
2,4-dichloro-5-pyrimidinecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-formamide With boric acid; trichlorophosphate at 5℃; for 0.5h; Stage #2: uridine at 5℃; for 2h; Reagent/catalyst; Temperature; | 96.6% |
4-morpholinecarboxaldehyde
2,4-dichloro-5-bromopyrimidine
2,4-dichloro-5-pyrimidinecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,4-dichloro-5-bromopyrimidine With TurboGrignard In tetrahydrofuran at -78 - -42℃; for 1.25h; Stage #2: 4-morpholinecarboxaldehyde In tetrahydrofuran at -78 - -42℃; for 3.91667h; | 87% |
Stage #1: 2,4-dichloro-5-bromopyrimidine With TurboGrignard In tetrahydrofuran at 78℃; for 1h; Stage #2: 4-morpholinecarboxaldehyde In tetrahydrofuran at -78 - -35℃; for 1.5h; Stage #3: With hydrogenchloride; water In tetrahydrofuran at -35℃; | 71% |
2,4-dihydroxypyrimidine-5-carbaldehyde
2,4-dichloro-5-pyrimidinecarboxaldehyde
Conditions | Yield |
---|---|
With triethylamine; trichlorophosphate at 30 - 35℃; for 3.5h; | 69% |
With trichlorophosphate at 80℃; for 0.5h; | 8.1 g |
2,4-dichloro-5-bromopyrimidine
N,N-dimethyl-formamide
2,4-dichloro-5-pyrimidinecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,4-dichloro-5-bromopyrimidine With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - -35℃; for 4h; | 31% |
Stage #1: 2,4-dichloro-5-bromopyrimidine With hydrogenchloride In tetrahydrofuran at -78 - 35℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 2h; | 28% |
Methyl formate
2,4-dichloro-5-iodopyrimidine
2,4-dichloro-5-pyrimidinecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,4-dichloro-5-iodopyrimidine With n-butyllithium In diethyl ether; hexane at -78℃; for 0.333333h; Inert atmosphere; Stage #2: Methyl formate In diethyl ether; hexane at -78℃; for 0.166667h; Inert atmosphere; |
N,N-dimethyl-formamide
uracil
A
2,6-Dichloropyrimidine
B
2,4-dichloro-5-pyrimidinecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at -5 - 5℃; for 0.5h; Stage #2: uracil at 5℃; for 2h; Temperature; |
5-hydroxymethyl uracil
2,4-dichloro-5-pyrimidinecarboxaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dipotassium peroxodisulfate; silver nitrate / water 2: trichlorophosphate; triethylamine / 3.5 h / 30 - 35 °C View Scheme |
2,4-dichloro-5-pyrimidinecarboxaldehyde
methylmagnesium bromide
1-(2,4-dichloropyrimidin-5-yl)ethanol
Conditions | Yield |
---|---|
Stage #1: 2,4-dichloro-5-pyrimidinecarboxaldehyde; methylmagnesium bromide In tetrahydrofuran; diethyl ether at -78℃; for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether; water | 97% |
2,4-dichloro-5-pyrimidinecarboxaldehyde
2-hydroxypropanedinitrile
Conditions | Yield |
---|---|
With dmap; ammonium chloride In acetonitrile at 10℃; for 1.33333h; | 85% |
2,4-dichloro-5-pyrimidinecarboxaldehyde
N-cyclopentylglycine ethyl ester
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl-formamide at 20℃; | 84% |
2,4-dichloro-5-pyrimidinecarboxaldehyde
6-chloro-1H-pyrazolo[3,4-d]pyrimidine
Conditions | Yield |
---|---|
With hydrazine In tetrahydrofuran at 20℃; for 0.5h; | 82% |
With hydrazine hydrate; triethylamine In tetrahydrofuran at 20℃; for 1h; | 68% |
With hydrazine hydrate In tetrahydrofuran at 0 - 20℃; for 0.5h; | 57% |
With hydrazine hydrate In tetrahydrofuran at 0 - 20℃; for 1.25h; | 50% |
With hydrazine In tetrahydrofuran at 20℃; for 1h; | 34% |
2,4-dichloro-5-pyrimidinecarboxaldehyde
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl-formamide at 20℃; | 82% |
methanol
2,4-dichloro-5-pyrimidinecarboxaldehyde
2-hydroxypropanedinitrile
Conditions | Yield |
---|---|
With dmap; acetic acid at 50℃; for 0.666667h; | 80% |
2,4-dichloro-5-pyrimidinecarboxaldehyde
ethanol
2-hydroxypropanedinitrile
Conditions | Yield |
---|---|
With dmap; acetic acid at 10℃; for 0.666667h; | 77% |
2,4-dichloro-5-pyrimidinecarboxaldehyde
isopropyl alcohol
2-hydroxypropanedinitrile
Conditions | Yield |
---|---|
With dmap; acetic acid at 10℃; for 0.666667h; | 77% |
methanol
2,4-dichloro-5-pyrimidinecarboxaldehyde
trimethyl orthoformate
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate at 65℃; for 14h; | 75% |
2,4-dichloro-5-pyrimidinecarboxaldehyde
6-chloro-1-(3-nitrobenzyl)-1H-pyrazolo[3,4-d]pyrimidine
Conditions | Yield |
---|---|
Stage #1: 2,4-dichloro-5-pyrimidinecarboxaldehyde In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 3-nitrobenzylhydrazine dihydrochloride In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere; | 62% |
2,4-dichloro-5-pyrimidinecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,4-dichloro-5-pyrimidinecarboxaldehyde In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 4-nitrobenzylhydrazine dihydrochloride In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere; | 56% |
2,4-dichloro-5-pyrimidinecarboxaldehyde
N1‐cyclopropyl‐4,5‐difluorobenzene‐1,2‐diamine
Conditions | Yield |
---|---|
With Oxone In water; N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; | 38% |
2,4-dichloro-5-pyrimidinecarboxaldehyde
Methyl thioglycolate
Conditions | Yield |
---|---|
Stage #1: 2,4-dichloro-5-pyrimidinecarboxaldehyde; Methyl thioglycolate With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 120℃; for 1.5h; | 32% |
2,4-dichloro-5-pyrimidinecarboxaldehyde
4-amino-3-(cyclopropylamino)benzonitrile
Conditions | Yield |
---|---|
With Oxone In water; N,N-dimethyl-formamide at 20℃; for 5h; Time; | 31% |
2,4-dichloro-5-pyrimidinecarboxaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrazine / tetrahydrofuran / 1 h / 20 °C 2: ammonium formate / palladium 10% on activated carbon / methanol / 4 h / Reflux View Scheme |
2,4-dichloro-5-pyrimidinecarboxaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrazine / tetrahydrofuran / 1 h / 20 °C 2: ammonium formate / palladium 10% on activated carbon / methanol / 4 h / Reflux 3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 16 h / 20 °C View Scheme |
2,4-dichloro-5-pyrimidinecarboxaldehyde
allyl bromide
Conditions | Yield |
---|---|
With indium; sodium iodide In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere; | 120 mg |
2,4-dichloro-5-pyrimidinecarboxaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: indium; sodium iodide / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere 2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / 50 °C / Inert atmosphere View Scheme |
2,4-dichloro-5-pyrimidinecarboxaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 1.2: 1.5 h / 120 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 25 °C View Scheme |
2,4-dichloro-5-pyrimidinecarboxaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 1.2: 1.5 h / 120 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 25 °C 3.1: ammonium hydroxide / tetrahydrofuran / 5 h / 0 - 10 °C View Scheme |
2,4-dichloro-5-pyrimidinecarboxaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 1.2: 1.5 h / 120 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 25 °C 3.1: ammonium hydroxide / tetrahydrofuran / 5 h / 0 - 10 °C 4.1: water; sodium hydroxide / ethanol / 1 h / 80 °C 4.2: pH 1 View Scheme |
2,4-dichloro-5-pyrimidinecarboxaldehyde
6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrazine hydrate / tetrahydrofuran / 0.5 h / 0 - 20 °C 2: toluene-4-sulfonic acid / dichloromethane / 20 °C View Scheme |
2,4-dichloro-5-pyrimidinecarboxaldehyde
6-(3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrazine hydrate / tetrahydrofuran / 0.5 h / 0 - 20 °C 2: toluene-4-sulfonic acid / dichloromethane / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / 1,4-dioxane / 1.5 h / 110 °C / Microwave irradiation View Scheme |
2,4-dichloro-5-pyrimidinecarboxaldehyde
6-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: hydrazine hydrate / tetrahydrofuran / 0.5 h / 0 - 20 °C 2: toluene-4-sulfonic acid / dichloromethane / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / 1,4-dioxane / 1.5 h / 110 °C / Microwave irradiation 4: sulfuryl dichloride / dichloromethane / 4 h / 0 - 20 °C View Scheme |
2,4-dichloro-5-pyrimidinecarboxaldehyde
6-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: hydrazine hydrate / tetrahydrofuran / 0.5 h / 0 - 20 °C 2: toluene-4-sulfonic acid / dichloromethane / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / 1,4-dioxane / 1.5 h / 110 °C / Microwave irradiation 4: sulfuryl dichloride / dichloromethane / 4 h / 0 - 20 °C 5: N-iodo-succinimide / N,N-dimethyl-formamide / 80 °C View Scheme |
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