N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 9-azabicyclo<3.3.1>nonane-N-oxyl In acetonitrile at 20 - 50℃; for 2h; Sealed tube; | 99% |
With fluorosulfonyl fluoride; potassium carbonate; dimethyl sulfoxide at 20℃; for 2h; Sealed tube; chemoselective reaction; | 99% |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(II) nitrate trihydrate In 2-methyltetrahydrofuran at 40℃; for 18h; Temperature; Reagent/catalyst; Solvent; | 99% |
4-(4-fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl)amino]pyrimidine-5-carbonitrile
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
With formic acid for 2h; Time; Reflux; | 95% |
With diisobutylaluminium hydride In toluene at -5℃; for 1h; | 81% |
Stage #1: 4-(4-fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl)amino]pyrimidine-5-carbonitrile With diisobutylaluminium hydride In dichloromethane at 0 - 5℃; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane; water at 0 - 30℃; | 80.3% |
N-[5-[1,3]dioxolane-2-yl-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
With acetic acid In water at 60 - 70℃; for 0.166667h; | 93% |
N-[5-(bromomethyl)-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Stage #1: N-[5-(bromomethyl)-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide With sodium hydrogencarbonate; dimethyl sulfoxide; sodium iodide for 25h; Kornblum Oxydation; Stage #2: With acetic anhydride; dimethyl sulfoxide at 70℃; | 93% |
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; water / acetonitrile / 4 h / Reflux 2: acetic anhydride; dimethyl sulfoxide / 85 °C View Scheme | |
Multi-step reaction with 2 steps 1: water / tetrahydrofuran / 6 h / Reflux 2: acetic anhydride; dimethyl sulfoxide / 17 h / 85 °C View Scheme |
A
tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate
B
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Stage #1: C29H40FN3O6S With ozone In methanol; dichloromethane at 25℃; for 5h; Stage #2: With thiourea In methanol; dichloromethane; water Temperature; Time; | A n/a B 82.2% |
ethyl 2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-carboxylic acid
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
With lithium borohydride In tetrahydrofuran at 0 - 5℃; for 4h; | 80% |
Multi-step reaction with 2 steps 1: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 2: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h View Scheme |
4-(4-fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methanesulfonyl)amino]pyrimidine
N,N-dimethyl-formamide
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
With trichlorophosphate at 90 - 108℃; Temperature; | 72% |
With trichlorophosphate at 90 - 108℃; | 72% |
4-(4-fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methanesulfonyl)amino]pyrimidine
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
With N,N-dimethyl-formamide; trichlorophosphate at 90 - 108℃; Temperature; Concentration; | 72% |
4-(4-fluorophenyl)-6-isopropyl-2-(methylamino)pyrimidine-5-carbaldehyde
methanesulfonyl chloride
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Stage #1: 4-(4-fluorophenyl)-6-isopropyl-2-(methylamino)pyrimidine-5-carbaldehyde With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: methanesulfonyl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 3.5h; | 55% |
Stage #1: 4-(4-fluorophenyl)-6-isopropyl-2-(methylamino)pyrimidine-5-carbaldehyde With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: methanesulfonyl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 3.5h; Product distribution / selectivity; | 55% |
With triethylamine In dichloromethane at 0 - 20℃; for 2h; Product distribution / selectivity; | 30% |
N-(4-(4-fluorophenyl)-6-isopropyl-5-(prop-1-enyl)pyrimidin-2-yl)-N-methylmethanesulfonamide
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
With oxone; water; sodium hydrogencarbonate; ruthenium(III) trichloride hydrate In acetonitrile at 20℃; for 24h; | 40% |
With Oxone; sodium hydrogencarbonate; ruthenium(III) trichloride hydrate In water; acetonitrile at 20℃; for 24h; | 40% |
4-fluorobenzaldehyde
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 86.7 percent / piperidine, AcOH / benzene / Heating 2: 1.) HMPA, 2.) DDQ / 1.) 100 deg C, 22 h, 2.) benzene, 30 min 3: 95.7 percent / m-CPBA / CHCl3 / Ambient temperature 4: 46.9 g / ethanol / 1 h / Ambient temperature 5: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 6: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 7: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h View Scheme |
(E)-2-<(4-fluorophenyl)methylene>-4-methyl-3-oxopentanoic acid ethyl ester
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 1.) HMPA, 2.) DDQ / 1.) 100 deg C, 22 h, 2.) benzene, 30 min 2: 95.7 percent / m-CPBA / CHCl3 / Ambient temperature 3: 46.9 g / ethanol / 1 h / Ambient temperature 4: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 5: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 6: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h View Scheme |
ethyl 4-methyl-3-oxo-pentanoate
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 86.7 percent / piperidine, AcOH / benzene / Heating 2: 1.) HMPA, 2.) DDQ / 1.) 100 deg C, 22 h, 2.) benzene, 30 min 3: 95.7 percent / m-CPBA / CHCl3 / Ambient temperature 4: 46.9 g / ethanol / 1 h / Ambient temperature 5: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 6: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 7: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h View Scheme |
5-ethoxycarbonyl-6-(4'-fluorophenyl)-4-isopropyl-2-(methylamino)pyrimidine
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 2: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 3: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h View Scheme |
ethyl 4-(4-fluorophenyl)-2-(methylsulfanyl)-6-(propan-2-yl)-pyrimidine-5-carboxylate
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 95.7 percent / m-CPBA / CHCl3 / Ambient temperature 2: 46.9 g / ethanol / 1 h / Ambient temperature 3: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 4: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 5: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h View Scheme |
ethyl 4-(4-fluorophenyl)-6-isopropyl-2-(methylsulfonyl)pyrimidine-5-carboxylate
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 46.9 g / ethanol / 1 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 3: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 4: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h View Scheme |
1-(4-Fluorophenyl)-3-isopropylpropan-1,3-dione
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 24 h / 20 °C 2: caesium carbonate / 2-methyltetrahydrofuran / 10 h / 40 °C 3: triethylamine / dichloromethane / 8 h / -5 °C / Inert atmosphere 4: N-Bromosuccinimide / acetonitrile / 0.5 h / UV-irradiation; Inert atmosphere; Sealed flow reactor 5: sodium hydrogencarbonate; water / acetonitrile / 4 h / Reflux 6: acetic anhydride; dimethyl sulfoxide / 85 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium carbonate / acetone / 24 h / 20 °C 2.1: caesium carbonate / 2-methyltetrahydrofuran / 10 h / 40 °C 3.1: triethylamine / dichloromethane / 8 h / -5 °C / Inert atmosphere 4.1: N-Bromosuccinimide / acetonitrile / 0.5 h / UV-irradiation; Inert atmosphere; Sealed flow reactor 5.1: sodium hydrogencarbonate; dimethyl sulfoxide / sodium iodide / 25 h 5.2: 70 °C View Scheme | |
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 4.17 h / 20 °C 2: sodium hydride / tetrahydrofuran; mineral oil / 48 h / 25 °C 3: triethylamine / dichloromethane / 17 h / -5 °C / Inert atmosphere 4: potassium hydroxide / Aliquat 336 / toluene / 24 h / 20 °C 5: oxone; sodium hydrogencarbonate; water / ruthenium(III) trichloride hydrate / acetonitrile / 24 h / 20 °C View Scheme |
4-(4-fluorophenyl)-6-isopropyl-N,5-dimethylpyrimidin-2-amine
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 8 h / -5 °C / Inert atmosphere 2: N-Bromosuccinimide / acetonitrile / 0.5 h / UV-irradiation; Inert atmosphere; Sealed flow reactor 3: sodium hydrogencarbonate; water / acetonitrile / 4 h / Reflux 4: acetic anhydride; dimethyl sulfoxide / 85 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 8 h / -5 °C / Inert atmosphere 2.1: N-Bromosuccinimide / acetonitrile / 0.5 h / UV-irradiation; Inert atmosphere; Sealed flow reactor 3.1: sodium hydrogencarbonate; dimethyl sulfoxide / sodium iodide / 25 h 3.2: 70 °C View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 8 h / -5 °C / Inert atmosphere 2: N-Bromosuccinimide / acetonitrile / 16 h / 20 °C / Inert atmosphere; UV-irradiation 3: sodium hydrogencarbonate; dimethyl sulfoxide; sodium iodide / 71 h / 20 °C / Inert atmosphere 4: acetic anhydride; dimethyl sulfoxide / 17 h / 85 °C View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 8 h / -5 °C / Inert atmosphere 2: N-Bromosuccinimide / acetonitrile / 16 h / 20 °C / Inert atmosphere; UV-irradiation 3: water / tetrahydrofuran / 6 h / Reflux 4: acetic anhydride; dimethyl sulfoxide / 17 h / 85 °C View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 26 h / 0 - 20 °C 2: N-Bromosuccinimide / acetonitrile / 68 h / 20 °C / UV-irradiation 3: sodium hydrogencarbonate / acetonitrile / 4 h / Reflux 4: acetic anhydride; dimethyl sulfoxide / 17 h / 85 °C View Scheme |
N-(4-(4-fluorophenyl)-6-isopropyl-5-methylpyrimidin-2-yl)-N-methylmethanesulfonamide
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / acetonitrile / 0.5 h / UV-irradiation; Inert atmosphere; Sealed flow reactor 2: sodium hydrogencarbonate; water / acetonitrile / 4 h / Reflux 3: acetic anhydride; dimethyl sulfoxide / 85 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / acetonitrile / 0.5 h / UV-irradiation; Inert atmosphere; Sealed flow reactor 2.1: sodium hydrogencarbonate; dimethyl sulfoxide / sodium iodide / 25 h 2.2: 70 °C View Scheme | |
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / acetonitrile / 16 h / 20 °C / Inert atmosphere; UV-irradiation 2: sodium hydrogencarbonate; dimethyl sulfoxide; sodium iodide / 71 h / 20 °C / Inert atmosphere 3: acetic anhydride; dimethyl sulfoxide / 17 h / 85 °C View Scheme | |
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / acetonitrile / 16 h / 20 °C / Inert atmosphere; UV-irradiation 2: water / tetrahydrofuran / 6 h / Reflux 3: acetic anhydride; dimethyl sulfoxide / 17 h / 85 °C View Scheme | |
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / acetonitrile / 68 h / 20 °C / UV-irradiation 2: sodium hydrogencarbonate / acetonitrile / 4 h / Reflux 3: acetic anhydride; dimethyl sulfoxide / 17 h / 85 °C View Scheme |
2-allyl-1-(4-fluorophenyl)-4-methylpentane-1,3-dione
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sodium hydride / tetrahydrofuran; mineral oil / 48 h / 25 °C 2: triethylamine / dichloromethane / 17 h / -5 °C / Inert atmosphere 3: potassium hydroxide / Aliquat 336 / toluene / 24 h / 20 °C 4: oxone; sodium hydrogencarbonate; water / ruthenium(III) trichloride hydrate / acetonitrile / 24 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / 0.33 h / 20 °C 1.2: 48.16 h / 25 °C 2.1: triethylamine / dichloromethane / 17 h / -5 °C 3.1: potassium hydroxide / Aliquat 336 / toluene / 24 h / 20 °C 4.1: sodium hydrogencarbonate; Oxone / ruthenium(III) trichloride hydrate / acetonitrile; water / 24 h / 20 °C View Scheme |
5-allyl-4-(4-fluorophenyl)-6-isopropyl-N-methylpyrimidin-2-amine
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 17 h / -5 °C / Inert atmosphere 2: potassium hydroxide / Aliquat 336 / toluene / 24 h / 20 °C 3: oxone; sodium hydrogencarbonate; water / ruthenium(III) trichloride hydrate / acetonitrile / 24 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 17 h / -5 °C 2: potassium hydroxide / Aliquat 336 / toluene / 24 h / 20 °C 3: sodium hydrogencarbonate; Oxone / ruthenium(III) trichloride hydrate / acetonitrile; water / 24 h / 20 °C View Scheme |
N-(5-allyl-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide / Aliquat 336 / toluene / 24 h / 20 °C 2: oxone; sodium hydrogencarbonate; water / ruthenium(III) trichloride hydrate / acetonitrile / 24 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium hydroxide / Aliquat 336 / toluene / 24 h / 20 °C 2: sodium hydrogencarbonate; Oxone / ruthenium(III) trichloride hydrate / acetonitrile; water / 24 h / 20 °C View Scheme |
1-(4-fluorophenyl)-2-methyl-3-isopropylpropan-1,3-dione
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: caesium carbonate / 2-methyltetrahydrofuran / 10 h / 40 °C 2: triethylamine / dichloromethane / 8 h / -5 °C / Inert atmosphere 3: N-Bromosuccinimide / acetonitrile / 0.5 h / UV-irradiation; Inert atmosphere; Sealed flow reactor 4: sodium hydrogencarbonate; water / acetonitrile / 4 h / Reflux 5: acetic anhydride; dimethyl sulfoxide / 85 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: caesium carbonate / 2-methyltetrahydrofuran / 10 h / 40 °C 2.1: triethylamine / dichloromethane / 8 h / -5 °C / Inert atmosphere 3.1: N-Bromosuccinimide / acetonitrile / 0.5 h / UV-irradiation; Inert atmosphere; Sealed flow reactor 4.1: sodium hydrogencarbonate; dimethyl sulfoxide / sodium iodide / 25 h 4.2: 70 °C View Scheme | |
Multi-step reaction with 5 steps 1: potassium tert-butylate / tert-butyl alcohol / 24 h / 70 °C 2: triethylamine / dichloromethane / 8 h / -5 °C / Inert atmosphere 3: N-Bromosuccinimide / acetonitrile / 16 h / 20 °C / Inert atmosphere; UV-irradiation 4: sodium hydrogencarbonate; dimethyl sulfoxide; sodium iodide / 71 h / 20 °C / Inert atmosphere 5: acetic anhydride; dimethyl sulfoxide / 17 h / 85 °C View Scheme |
N-(4-(4-fluorophenyl)-6-isopropyl-5-methylpyrimidin-2-yl)-N-methylmethanesulfonamide
A
N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
B
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / acetonitrile / 16 h / 20 °C / Inert atmosphere; UV-irradiation 2: sodium hydrogencarbonate; dimethyl sulfoxide; sodium iodide / 71 h / 20 °C / Inert atmosphere View Scheme |
N-[5-(bromomethyl)-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
A
N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
B
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; dimethyl sulfoxide; sodium iodide at 20℃; for 71h; Kornblum oxidation; Inert atmosphere; |
1-(4-fluorophenyl)-2-methyl-3-isopropylpropan-1,3-dione
A
N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
B
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium tert-butylate / tert-butyl alcohol / 24 h / 70 °C 2: triethylamine / dichloromethane / 8 h / -5 °C / Inert atmosphere 3: N-Bromosuccinimide / acetonitrile / 16 h / 20 °C / Inert atmosphere; UV-irradiation 4: sodium hydrogencarbonate; dimethyl sulfoxide; sodium iodide / 71 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1: caesium carbonate / 2-methyltetrahydrofuran / 24 h / 70 °C 2: triethylamine / dichloromethane / 8 h / -5 °C / Inert atmosphere 3: N-Bromosuccinimide / acetonitrile / 16 h / 20 °C / Inert atmosphere; UV-irradiation 4: sodium hydrogencarbonate; dimethyl sulfoxide; sodium iodide / 71 h / 20 °C / Inert atmosphere View Scheme |
4-(4-fluorophenyl)-6-isopropyl-N,5-dimethylpyrimidin-2-amine
A
N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
B
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 8 h / -5 °C / Inert atmosphere 2: N-Bromosuccinimide / acetonitrile / 16 h / 20 °C / Inert atmosphere; UV-irradiation 3: sodium hydrogencarbonate; dimethyl sulfoxide; sodium iodide / 71 h / 20 °C / Inert atmosphere View Scheme |
1-(4-Fluorophenyl)-3-isopropylpropan-1,3-dione
A
N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
B
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 48 h / 20 °C / Inert atmosphere 2: potassium tert-butylate / tert-butyl alcohol / 24 h / 70 °C 3: triethylamine / dichloromethane / 8 h / -5 °C / Inert atmosphere 4: N-Bromosuccinimide / acetonitrile / 16 h / 20 °C / Inert atmosphere; UV-irradiation 5: sodium hydrogencarbonate; dimethyl sulfoxide; sodium iodide / 71 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 48 h / 20 °C / Inert atmosphere 2: caesium carbonate / 2-methyltetrahydrofuran / 24 h / 70 °C 3: triethylamine / dichloromethane / 8 h / -5 °C / Inert atmosphere 4: N-Bromosuccinimide / acetonitrile / 16 h / 20 °C / Inert atmosphere; UV-irradiation 5: sodium hydrogencarbonate; dimethyl sulfoxide; sodium iodide / 71 h / 20 °C / Inert atmosphere View Scheme |
Methyl 4-methyl-3-oxopentanoate
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: dmap; ammonia / toluene; water / 0 - 35 °C / Inert atmosphere 2.1: copper(l) chloride; sulfuric acid / methanol / 30 - 70 °C / Inert atmosphere; Reflux 3.1: potassium carbonate; tert.-butylhydroperoxide; copper(II) choride dihydrate / dichloromethane / 25 - 30 °C / Inert atmosphere 4.1: trichlorophosphate / dichloromethane / 0 - 105 °C / Inert atmosphere 5.1: potassium carbonate / toluene / 25 - 115 °C / Inert atmosphere; Reflux 6.1: diisobutylaluminium hydride / dichloromethane / 0 - 5 °C / Inert atmosphere 6.2: 0 - 30 °C View Scheme |
methyl (3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-6-triphenylphosphoranylidenehexanoate
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesulfonamido)-pyrimidin-5-yl)-(3R)-3-tert-butyldimethylsiloxy-5-oxo-(E)-6-heptenoic acid methyl ester
Conditions | Yield |
---|---|
In toluene for 30h; Wittig condensation; Heating / reflux; | 100% |
Stage #1: methyl (3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-6-triphenylphosphoranylidenehexanoate; N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide In acetonitrile for 10 - 12h; Heating / reflux; Stage #2: With acetic acid In di-isopropyl ether; water at 20℃; for 0.25h; Stage #3: With water; sodium hydrogencarbonate In di-isopropyl ether Product distribution / selectivity; | 100% |
In acetonitrile for 10 - 12h; Product distribution / selectivity; Heating / reflux; | 100% |
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate In tetrahydrofuran at 5 - 25℃; for 2h; | 98% |
With methanol; sodium tetrahydroborate In tetrahydrofuran at 5 - 10℃; | |
With methanol; sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 1h; |
methyl (triphenylphosphoranylidene)acetate
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
methyl 3-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-(2E)-propenoate
Conditions | Yield |
---|---|
In acetonitrile at 20 - 81℃; | 96% |
thiosemicarbazide
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Stage #1: thiosemicarbazide; allyl halide In ethanol for 3h; Reflux; Stage #2: N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide In ethanol for 5h; Reflux; | 93% |
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
In acetonitrile at 50℃; for 3h; Wittig Olefination; | 92.9% |
thiosemicarbazide
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Stage #1: thiosemicarbazide; isopentyl halide In ethanol for 3h; Reflux; Stage #2: N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide In ethanol for 6h; Reflux; | 92% |
[(4R,6S)-2,2-dimethyl-6-(1-phenyl-1H-tetrazole-5-sulfonylmethyl)[1,3]dioxan-4-yl]acetic acid tert-butyl ester
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid tert butyl ester
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran; water at -15 - 42℃; for 1h; Temperature; Inert atmosphere; | 91% |
With sodium hydride In tetrahydrofuran at 0 - 35℃; Solvent; Temperature; Reagent/catalyst; | 120 g |
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
In acetonitrile at 50℃; for 3h; Wittig Olefination; | 90.6% |
(R)-methyl 3-(tert-butyldimethylsilyloxy)-5-oxohexanoate
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Stage #1: N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide With tin(IV) chloride In tetrahydrofuran; dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: (R)-methyl 3-(tert-butyldimethylsilyloxy)-5-oxohexanoate With 4-methyl-morpholine In tetrahydrofuran; dichloromethane at 0℃; for 3h; Reagent/catalyst; Inert atmosphere; | 87% |
thiosemicarbazide
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Stage #1: thiosemicarbazide; benzyl halide In ethanol for 3h; Reflux; Stage #2: N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide In ethanol for 6h; Reflux; | 85% |
thiosemicarbazide
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Stage #1: thiosemicarbazide; n-heptyl halide In ethanol for 3h; Reflux; Stage #2: N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide In ethanol for 6h; Reflux; | 85% |
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran; tert-butyl alcohol at -40℃; for 4h; | 85% |
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid tert butyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran at 42℃; Inert atmosphere; | 84.5% |
thiosemicarbazide
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Stage #1: thiosemicarbazide; isopropyl halide In ethanol for 3h; Reflux; Stage #2: N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide In ethanol for 5.5h; Reflux; | 83% |
allyl bromide
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
N-[4-(4-fluorophenyl)-5-(1-hydroxybut-3-enyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
Conditions | Yield |
---|---|
Stage #1: allyl bromide With magnesium In diethyl ether for 0.5h; Inert atmosphere; Stage #2: N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide In tetrahydrofuran; diethyl ether at -5 - 5℃; Stage #3: With hydrogenchloride; water In tetrahydrofuran; diethyl ether for 0.5h; | 81% |
Molecular structure of 4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl)amino]pyrimidinyl-5-yl-formyl (CAS NO.147118-37-4) is:
Product Name: 4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl)amino]pyrimidinyl-5-yl-formyl
CAS Registry Number: 147118-37-4
Molecular Formula: C16H18FN3O3S
Molecular Weight: 351.39
Surface Tension: 53.975 dyne/cm
Density: 1.32 g/cm3
Flash Point: 278.322 °C
Enthalpy of Vaporization: 81.332 kJ/mol
Boiling Point: 536.594 °C at 760 mmHg
Product Categories: Rosuvastatin Calcium and its intermediates
4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl)amino]pyrimidinyl-5-yl-formyl , its cas register number is 147118-37-4. It also can be called Methanesulfonamide,N-[4-(4-fluorophenyl)-5-formyl-6-(1-methylethyl)-2-pyrimidinyl]-N-methyl- ; N-[4-(4-Fluorophenyl)-5-formyl-6-(1-methylethyl)-2-pyrimidinyl-N-methyl-methanesulfonamide .
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