147118-37-4

Basic information

• Product Name: 4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl)amino]pyrimidinyl-5-yl-formyl
• Synonyms: Methyl[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-sulfonyl-amino)-pyrimidin-5-yl]carboxylate;4-(4-Fluorophenyl)-5-brominemethyl-6-lsopropyl-2-(N-Methyl-N-Methylsulfonylamino)Pyrimidine;4-(4-Fluorophenyl)-6-Isopropyl-2-(N-Mehyl-N-Mehylsulfonylamino)Pyrimidine-5-yl-carboxaldehyde;4-(4-fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl)amino]pyrimine-5-yl-formyl;Z-8 ：4-(4-fluorophenyl)-6-isopropyl-2- [(N-methyl-N- methylsulfonyl)amino]pyriminl-5-yl-formyl;4-(4-fluorophenyl)-6-isopropyl-2-[(n-methyl-n-methylsulfonyl)amino]pyriminl-5-yl-;4-(4-fluorophenyl)-6-isopropyl-2-[(n-methyl-n-methylsulfonyl)amino]pyriminl-5-yl- formaldehyde;4-(4-Fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidine-5-carboxaldehyde ,98%
• CAS NO: 147118-37-4
• Molecular Formula: C₁₆H₁₈FN₃O₃S
• Molecular Weight: 351.4
• EINECS: 1806241-263-5
• Product Categories: Rosuvastatin Calcium and its intermediates;Rosuvastatin intermediates;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 147118-37-4.mol
• Article Data: 29

Chemical Properties

• Melting Point: 178.0 to 182.0 °C
• Boiling Point: 536.594 °C at 760 mmHg
• Flash Point: 278.322 °C
• Appearance: White/Solid
• Density: 1.32 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Very Slightly, Heated)
• PKA: -1.68±0.10(Predicted)
• CAS DataBase Reference: 4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl)amino]pyrimidinyl-5-yl-formyl(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl)amino]pyrimidinyl-5-yl-formyl(147118-37-4)
• EPA Substance Registry System: 4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methylsulfonyl)amino]pyrimidinyl-5-yl-formyl(147118-37-4)

Safety Data

• Hazardous Substances Data: 147118-37-4(Hazardous Substances Data)

Usage

Uses

Rosuvastatin intermediate.

InChI:InChI=1/C16H18FN3O3S/c1-10(2)14-13(9-21)15(11-5-7-12(17)8-6-11)19-16(18-14)20(3)24(4,22)23/h5-10H,1-4H3

Synthetic route

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide (147118-36-3) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (1092844-00-2) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (916480-94-9) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (799842-07-2) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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

C29H40FN3O6S → tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate (124752-23-4) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (147118-30-7) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (1031246-43-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (1031246-43-1) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

Conditions	Yield
With N,N-dimethyl-formamide; trichlorophosphate at 90 - 108℃; Temperature; Concentration;	72%

4-(4-fluorophenyl)-6-isopropyl-2-(methylamino)pyrimidine-5-carbaldehyde (147118-41-0) + methanesulfonyl chloride (124-63-0) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (1356998-77-0) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (459-57-4) + PhCH2CH2MgHal → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (122930-45-4) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (7152-15-0) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (147118-32-9) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (147118-27-2) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (147118-28-3) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (114433-94-2) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (1207460-34-1) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (953776-62-0) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (1356998-74-7) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (1356998-75-8) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (1356998-76-9) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (1354455-77-8) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (953776-62-0) → N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide (147118-36-3) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (799842-07-2) → N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide (147118-36-3) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (1354455-77-8) → N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide (147118-36-3) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (1207460-34-1) → N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide (147118-36-3) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (114433-94-2) → N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide (147118-36-3) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (42558-54-3) → N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4)

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 (147118-35-2) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4) → 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 (147118-38-5)

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 (147118-37-4) → N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide (147118-36-3)

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 (21204-67-1) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4) → methyl 3-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-(2E)-propenoate (1024024-26-7)

Conditions	Yield
In acetonitrile at 20 - 81℃;	96%

thiosemicarbazide (79-19-6) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4) + allyl halide → 2-[N-methyl (methylsulphanamid)]-4-[(4-fluorophenyl)-6-isopropylpyrimidine-5-yl] methyleneamino-2-allylisothiourea

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%

ethyl 2-((4R,6S)-6-triphenylphosphinomethylidene-2,2-dimethyl-1,3-dioxan-4-yl)acetate + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4) → C27H36FN3O6S

Conditions	Yield
In acetonitrile at 50℃; for 3h; Wittig Olefination;	92.9%

thiosemicarbazide (79-19-6) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4) + isopentyl halide → 2-[N-methyl (methylsulphanamid)]-4-[(4-fluorophenyl)-6-isopropylpyrimidine-5-yl] methyleneamino-2-isopentylisothiourea

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 (380460-37-7) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4) → 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 (289042-12-2)

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

ethyl 2-((4R,6S)-6-triphenylphosphinemethylidene-2-ethoxycarbonylmethyl-1,3-dioxane-4-yl)acetate + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4) → C29H38FN3O8S

Conditions	Yield
In acetonitrile at 50℃; for 3h; Wittig Olefination;	90.6%

(R)-methyl 3-(tert-butyldimethylsilyloxy)-5-oxohexanoate (1622874-01-4) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4) → methyl (3R,6E)-3-[[(1,1-dimethylethyl)dimethylsilyl]-oxo]-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-5-pyrimidyl]-5-oxo-6-heptenoate

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 (79-19-6) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4) + benzyl halide → 2-[N-methyl (methylsulphanamid)]-4-[(4-fluorophenyl)-6-isopropylpyrimidine-5-yl] methyleneamino-2-benzylisothiourea

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 (79-19-6) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4) + n-heptyl halide → 2-[N-methyl (methylsulphanamid)]-4-[(4-fluorophenyl)-6-isopropylpyrimidine-5-yl] methyleneamino-2-hepteneisothiourea

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%

C19H23N5O7S + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4) → C28H35FN4O7S

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; tert-butyl alcohol at -40℃; for 4h;	85%

1,1-dimethylethyl 2,4,6-trideoxy-3,5-O-(1-methylethylidene)-6-[(1-phenyl-1H-tetrazol-5-yl)sulfonyl]-D-erythro-hexonate + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4) → 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 (289042-12-2)

Conditions	Yield
In tetrahydrofuran at 42℃; Inert atmosphere;	84.5%

thiosemicarbazide (79-19-6) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4) + isopropyl halide → 2-[N-methyl(methylsulphanamid)] - 4-[(4-fluorophenyl)-6-isopropylpyrimidine-5-yl] methyleneamino-2-isopropylisothiourea

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 (106-95-6) + N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (147118-37-4) → N-[4-(4-fluorophenyl)-5-(1-hydroxybut-3-enyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide (1352138-41-0)

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%

Upstream product

• 147118-27-2 ethyl 4-(4-fluorophenyl)-2-(methylsulfanyl)-6-(propan-2-yl)-pyrimidine-5-carboxylate 
• 147118-28-3 ethyl 4-(4-fluorophenyl)-6-isopropyl-2-(methylsulfonyl)pyrimidine-5-carboxylate 
• 147118-30-7 ethyl 2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-carboxylic acid 
• 147118-41-0 4-(4-fluorophenyl)-6-isopropyl-2-(methylamino)pyrimidine-5-carbaldehyde 
• 124-63-0 methanesulfonyl chloride 
• 1354455-77-8 1-(4-fluorophenyl)-2-methyl-3-isopropylpropan-1,3-dione 
• 1356998-77-0 N-(4-(4-fluorophenyl)-6-isopropyl-5-(prop-1-enyl)pyrimidin-2-yl)-N-methylmethanesulfonamide 
• 1356998-76-9 N-(5-allyl-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide 
• 1356998-75-8 5-allyl-4-(4-fluorophenyl)-6-isopropyl-N-methylpyrimidin-2-amine 
• 1356998-74-7 2-allyl-1-(4-fluorophenyl)-4-methylpentane-1,3-dione 
• 953776-62-0 N-(4-(4-fluorophenyl)-6-isopropyl-5-methylpyrimidin-2-yl)-N-methylmethanesulfonamide 
• 1207460-34-1 4-(4-fluorophenyl)-6-isopropyl-N,5-dimethylpyrimidin-2-amine 
• 799842-07-2 N-[5-(bromomethyl)-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide 
• 114433-94-2 1-(4-Fluorophenyl)-3-isopropylpropan-1,3-dione 

Downstream Products

• 147118-38-5 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 
• 910867-07-1 ethyl (E)-3-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesulfonamido)pyrimidin-5-yl]acrylate 
• 1031246-52-2 ethyl (3R,6E)-3-(tert-butyldiphenylsilyloxy)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methanesulfonyl)amino]pyrimidin-5-yl]-5-oxohept-6-enoate 
• 1024024-26-7 methyl 3-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-(2E)-propenoate 
• 1235588-97-2 tert-butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2-phenyl-1,3-dioxan-4-yl)acetate 
• 287714-41-4 rosuvastatin 
• 1422619-13-3 7-[4-(4-fluorophenyl)-6-isopropyl-2(N-methyl-N-methanesulfonamido)pyrimidin-5-yl]-(3R)-3-hydroxy-5-carbonyl-6-(E)-heptenoic acid 
• 1378943-63-5 C₂₉H₄₀FN₃O₆S 
• 1031246-31-7 4-(4-fluorophenyl)-N-methyl-6-(1-methylethyl)-2-pyrimidinamine 
• 1031246-43-1 4-(4-fluorophenyl)-6-isopropyl-2-[(N-methyl-N-methanesulfonyl)amino]pyrimidine 
• 289042-12-2 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 
• 852820-97-4 (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidine-5-yl]-3,5-dihydroxyhept-6-enoic acid isopropylamine 
• 503610-43-3 Rosuvastatin lactone 

Relevant articles and documents

An efficient approach to the key intermediate of rosuvastatin

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