6-ethyl-5-fluoropyrimidin-4(1H)-one
4-chloro-5-fluoro-6-ethylpyrimidine
Conditions | Yield |
---|---|
With triethylamine; trichlorophosphate In dichloromethane at 48℃; for 6h; Product distribution / selectivity; Industry scale; Heating / reflux; | 99% |
With triethylamine; trichlorophosphate In dichloromethane for 5h; Product distribution / selectivity; Heating / reflux; | 90% |
With triethylamine; trichlorophosphate In dichloromethane at 40℃; for 5.16667h; Reflux; |
6-ethyl-5-fluoro-4-hydroxypyrimidine
4-chloro-5-fluoro-6-ethylpyrimidine
Conditions | Yield |
---|---|
Stage #1: 6-ethyl-5-fluoro-4-hydroxypyrimidine With triethylamine; trichlorophosphate In dichloromethane for 5.5h; Heating / reflux; Stage #2: With hydrogenchloride; water In dichloromethane at 20℃; | 95% |
With triethylamine; trichlorophosphate In dichloromethane at 40℃; for 8h; Reflux; | 90% |
With trichlorophosphate In N,N-dimethyl-formamide at 90℃; for 5h; | 90.2% |
3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol
A
1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone
B
4-chloro-5-fluoro-6-ethylpyrimidine
Conditions | Yield |
---|---|
With hydrogenchloride In water at 60 - 70℃; Temperature; Reagent/catalyst; Solvent; | A 88.4% B n/a |
6-Ethyl-5-fluoropyrimidin-4(3H)-one
4-chloro-5-fluoro-6-ethylpyrimidine
Conditions | Yield |
---|---|
With trichlorophosphate Heating; |
2-fluoro-3-oxopentanoic acid ethyl ester
4-chloro-5-fluoro-6-ethylpyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1) MeONa, MeOH 2: POCl3 / Heating View Scheme | |
Multi-step reaction with 2 steps 1: sodium methylate / methanol / 20 h / 15 °C 2: trichlorophosphate / 3 h / 60 °C View Scheme |
4-chloro-5-fluoro-6-ethylpyrimidine
1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane
Conditions | Yield |
---|---|
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In dichloromethane at 55℃; for 16h; Temperature; | 98% |
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In dichloromethane for 12h; Reflux; | 95.1% |
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In dichloromethane for 12h; Reflux; | 95.1% |
p-Chlorothiophenol
4-chloro-5-fluoro-6-ethylpyrimidine
4-(4-chloro-phenylsulfanyl)-6-ethyl-5-fluoropyrimidine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 10 - 20℃; for 2h; | 96% |
4-chloro-5-fluoro-6-ethylpyrimidine
Methyl thiosalicylate
methyl 2-(6-ethyl-5-fluoropyrimidin-4-yl-sulfanyl)benzoate
Conditions | Yield |
---|---|
Stage #1: Methyl thiosalicylate With sodium hydride In tetrahydrofuran at 5℃; for 0.666667h; Stage #2: 4-chloro-6-ethyl-5-fluoropyrimidine In tetrahydrofuran at 20 - 25℃; | 96% |
thiophenol
4-chloro-5-fluoro-6-ethylpyrimidine
4-(phenylsulfanyl)-6-ethyl-5-fluoropyrimidine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 10℃; for 2h; | 95% |
4-chloro-5-fluoro-6-ethylpyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 120℃; for 17.3h; Sealed tube; | 81% |
4-chloro-5-fluoro-6-ethylpyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 120℃; for 18h; Sealed tube; | 74% |
4-chloro-5-fluoro-6-ethylpyrimidine
6-ethyl-5-fluoropyrimidine-4-thiol
Conditions | Yield |
---|---|
With sodium hydrogensulfide In acetonitrile at 48 - 52℃; for 8.75h; Product distribution / selectivity; Industry scale; | 73% |
With sodium hydrogensulfide In methanol at 50℃; for 4.25h; Product distribution / selectivity; |
1-methyl-5-mercaptotetrazole
4-chloro-5-fluoro-6-ethylpyrimidine
Conditions | Yield |
---|---|
Stage #1: 1-methyl-5-mercaptotetrazole With sodium hydride In tetrahydrofuran at 5 - 25℃; Stage #2: 4-chloro-6-ethyl-5-fluoropyrimidine In tetrahydrofuran at 5 - 25℃; | 63.4% |
4-chloro-5-fluoro-6-ethylpyrimidine
dl-α-methyl-4-pentafluorophenoxybenzylamine
Conditions | Yield |
---|---|
With triethylamine; dmap In N,N-dimethyl-formamide for 8h; Substitution; Heating; |
4-chloro-5-fluoro-6-ethylpyrimidine
dl-α-methyl-4-difluoromethoxybenzylamine
Conditions | Yield |
---|---|
With triethylamine at 20℃; Substitution; |
4-chloro-5-fluoro-6-ethylpyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: LDA / tetrahydrofuran 2: H2, AcONa / Pd/C / ethanol / 20 °C View Scheme |
4-chloro-5-fluoro-6-ethylpyrimidine
voriconazole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: LDA / tetrahydrofuran 2: H2, AcONa / Pd/C / ethanol / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: diisopropylamine; n-butyllithium / n-heptane; hexane; tetrahydrofuran / 0.25 h / -80 - -70 °C / Inert atmosphere 1.2: 2 h / -80 - -55 °C 1.3: -70 - -10 °C 2.1: sodium acetate / ethyl acetate; water / 0.5 h / 25 - 30 °C 2.2: 25 - 30 °C / 3677.86 Torr 2.3: 0.5 h / 20 - 25 °C 3.1: acetone; methanol / 15 h / -20 - 25 °C 4.1: sodium hydroxide / dichloromethane; water / 0.25 h / pH 11 - 14 View Scheme | |
Multi-step reaction with 5 steps 1.1: diisopropylamine; n-butyllithium / n-heptane; hexane; tetrahydrofuran / 0.25 h / -80 - -70 °C / Inert atmosphere 1.2: 2 h / -80 - -55 °C 1.3: -70 - -10 °C 2.1: hydrogen; sodium acetate / palladium 10% on activated carbon / ethyl acetate; water / 25 - 30 °C / 3677.86 Torr 2.2: 0.5 h / 20 - 25 °C 2.3: 12.5 h / 25 - 30 °C 3.1: sodium hydroxide / dichloromethane; water / 0.5 h / pH 9 - 12 4.1: acetone; methanol / 15 h / -20 - 25 °C 5.1: sodium hydroxide / dichloromethane; water / 0.25 h / pH 11 - 14 View Scheme |
4-chloro-5-fluoro-6-ethylpyrimidine
3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran; n-heptane at -70 - -65℃; for 3 - 4h; pH=5 - 8; |
1-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-5-yl]methanamine
4-chloro-5-fluoro-6-ethylpyrimidine
Conditions | Yield |
---|---|
Stage #1: 1-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-5-yl]methanamine; 4-chloro-6-ethyl-5-fluoropyrimidine With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 0℃; Stage #2: With hydrogenchloride In 1,4-dioxane; methanol |
4-chloro-5-fluoro-6-ethylpyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: diisopropylamine; n-butyllithium / n-heptane; hexane; tetrahydrofuran / 0.25 h / -80 - -70 °C / Inert atmosphere 1.2: 2 h / -80 - -55 °C 1.3: -70 - -10 °C 2.1: sodium acetate / ethyl acetate; water / 0.5 h / 25 - 30 °C 2.2: 25 - 30 °C / 3677.86 Torr 2.3: 0.5 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: diisopropylamine; n-butyllithium / n-heptane; hexane; tetrahydrofuran / 0.25 h / -80 - -70 °C / Inert atmosphere 1.2: 2 h / -80 - -55 °C 1.3: -70 - -10 °C 2.1: hydrogen; sodium acetate / palladium 10% on activated carbon / ethyl acetate; water / 25 - 30 °C / 3677.86 Torr 2.2: 0.5 h / 20 - 25 °C 2.3: 12.5 h / 25 - 30 °C 3.1: sodium hydroxide / dichloromethane; water / 0.5 h / pH 9 - 12 View Scheme | |
Multi-step reaction with 3 steps 1.1: diisopropylamine; n-butyllithium / n-heptane; hexane; tetrahydrofuran / 0.25 h / -80 - -70 °C / Inert atmosphere 1.2: 2 h / -80 - -55 °C 1.3: -70 - -10 °C 2.1: hydrogen; sodium acetate; sodium carbonate / palladium 10% on activated carbon / ethyl acetate; water / 25 - 30 °C / 3677.86 Torr 2.2: 0.5 h / 20 - 25 °C 2.3: 10 - 25 °C 3.1: potassium carbonate / dichloromethane; water / 0.5 h / pH 8 - 10 View Scheme |
4-chloro-5-fluoro-6-ethylpyrimidine
(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: diisopropylamine; n-butyllithium / n-heptane; hexane; tetrahydrofuran / 0.25 h / -80 - -70 °C / Inert atmosphere 1.2: 2 h / -80 - -55 °C 1.3: -70 - -10 °C 2.1: sodium acetate / ethyl acetate; water / 0.5 h / 25 - 30 °C 2.2: 25 - 30 °C / 3677.86 Torr 2.3: 0.5 h / 20 - 25 °C 3.1: acetone; methanol / 15 h / -20 - 25 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: diisopropylamine; n-butyllithium / n-heptane; hexane; tetrahydrofuran / 0.25 h / -80 - -70 °C / Inert atmosphere 1.2: 2 h / -80 - -55 °C 1.3: -70 - -10 °C 2.1: hydrogen; sodium acetate / palladium 10% on activated carbon / ethyl acetate; water / 25 - 30 °C / 3677.86 Torr 2.2: 0.5 h / 20 - 25 °C 2.3: 12.5 h / 25 - 30 °C 3.1: sodium hydroxide / dichloromethane; water / 0.5 h / pH 9 - 12 4.1: acetone; methanol / 15 h / -20 - 25 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: diisopropylamine; n-butyllithium / n-heptane; hexane; tetrahydrofuran / 0.25 h / -80 - -70 °C / Inert atmosphere 1.2: 2 h / -80 - -55 °C 1.3: -70 - -10 °C 2.1: hydrogen; sodium acetate; sodium carbonate / palladium 10% on activated carbon / ethyl acetate; water / 25 - 30 °C / 3677.86 Torr 2.2: 0.5 h / 20 - 25 °C 2.3: 10 - 25 °C 3.1: potassium carbonate / dichloromethane; water / 0.5 h / pH 8 - 10 4.1: acetone; methanol / 15 h / -20 - 25 °C View Scheme |
4-chloro-5-fluoro-6-ethylpyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: diisopropylamine; n-butyllithium / n-heptane; hexane; tetrahydrofuran / 0.25 h / -80 - -70 °C / Inert atmosphere 1.2: 2 h / -80 - -55 °C 1.3: -70 - -10 °C 2.1: hydrogen; sodium acetate; sodium carbonate / palladium 10% on activated carbon / ethyl acetate; water / 25 - 30 °C / 3677.86 Torr 2.2: 0.5 h / 20 - 25 °C 2.3: 10 - 25 °C View Scheme |
4-chloro-5-fluoro-6-ethylpyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: diisopropylamine; n-butyllithium / n-heptane; hexane; tetrahydrofuran / 0.25 h / -80 - -70 °C / Inert atmosphere 1.2: 2 h / -80 - -55 °C 1.3: -70 - -10 °C 2.1: hydrogen; sodium acetate / palladium 10% on activated carbon / ethyl acetate; water / 25 - 30 °C / 3677.86 Torr 2.2: 0.5 h / 20 - 25 °C 2.3: 12.5 h / 25 - 30 °C View Scheme |
4-chloro-5-fluoro-6-ethylpyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / dichloromethane / 16 h / Inert atmosphere; Reflux 2.1: lead; zinc; bromine / dichloromethane; tetrahydrofuran / 30 - 50 °C 2.2: 4 h / 20 - 25 °C View Scheme |
4-chloro-5-fluoro-6-ethylpyrimidine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / dichloromethane / 16 h / Inert atmosphere; Reflux 2.1: lead; zinc; bromine / dichloromethane; tetrahydrofuran / 30 - 50 °C 2.2: 4 h / 20 - 25 °C 3.1: sodium hydroxide / water; methanol / 20 - 25 °C / pH 8 - 9 3.2: 55 - 60 °C 3.3: 1 h / 40 - 45 °C View Scheme |
Structure of 4-Chloro-6-ethyl-5-fluoropyrimidine (CAS NO.137234-74-3):
Empirical Formula: C6H6ClFN2
Molecular Weight: 160.5766
Index of Refraction: 1.502
Molar Refractivity: 36.873 cm3
Molar Volume: 124.859 cm3
Polarizability: 14.618×10-24cm3
Surface Tension: 40.592 dyne/cm
Density: 1.286 g/cm3
Flash Point: 81.358 °C
Enthalpy of Vaporization: 42.896 kJ/mol
Boiling Point: 210.913 °C at 760 mmHg
Vapour Pressure: 0.272 mmHg at 25°C
Product Categories: APIs & Intermediate;Pyrimidine
Synonyms of 4-Chloro-6-ethyl-5-fluoropyrimidine (CAS NO.137234-74-3): Pyrimidine,4-chloro-6-ethyl-5-fluoro-
Risk Statements: 20/21/22-36/37/38
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-36/37/39-45
S22:Do not breathe dust.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
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