Product Name

  • Name

    4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-n-methylsulfonyl)amino]pyrimidine-5-yl-methanol

  • EINECS 604-563-9
  • CAS No. 147118-36-3
  • Article Data25
  • CAS DataBase
  • Density 1.317 g/cm3
  • Solubility
  • Melting Point
  • Formula C16H20FN3O3S
  • Boiling Point 538.273 °C at 760 mmHg
  • Molecular Weight 353.418
  • Flash Point 279.338 °C
  • Transport Information
  • Appearance White or off-white powder
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 147118-36-3 (4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-n-methylsulfonyl)amino]pyrimidine-5-yl-methanol)
  • Hazard Symbols
  • Synonyms 5-(Hydroxymethyl)-4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidine;Methanesulfonamide,N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(1-methylethyl)-2-pyrimidinyl]-N-methyl-;
  • PSA 91.77000
  • LogP 3.37500

Synthetic route

methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate
289042-11-1

methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Stage #1: methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate With diisobutylaluminium hydride In hexane; toluene at -10℃; for 1h;
Stage #2: With hydrogenchloride In methanol; hexane; water; toluene at -10 - 40℃; for 0.333333h;		100%
Stage #1: methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 0 - 60℃; for 20h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water for 1.5h; Temperature; Reagent/catalyst; Solvent;		96.7%
Stage #1: methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate With diisobutylaluminium hydride In toluene at -15 - -5℃; for 2 - 2.5h;
Stage #2: With hydrogenchloride; water In toluene at -10 - 40℃; for 1 - 1.33333h;
Stage #3: With sodium hydrogencarbonate In water; ethyl acetate Product distribution / selectivity;		93%
N-[5-(bromomethyl)-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
799842-07-2

N-[5-(bromomethyl)-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
With water In tetrahydrofuran for 6h; Reflux;100%
With oxygen; eosin y In dimethyl sulfoxide at 40℃; Irradiation;82%
With water; sodium hydrogencarbonate In acetonitrile for 4h; Reflux;
With water; sodium hydrogencarbonate In acetonitrile for 4h; Reflux;
With sodium hydrogencarbonate In acetonitrile for 4h; Reflux;
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
147118-37-4

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
147118-36-3

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
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;
4-(4-fluorophenyl)-6-isopropyl-2-(methanesulfonyl(methyl)amino)pyrimidine-5-carboxylic acid
1263475-93-9

4-(4-fluorophenyl)-6-isopropyl-2-(methanesulfonyl(methyl)amino)pyrimidine-5-carboxylic acid

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
With lithium borohydride; boron trifluoride diethyl etherate In tetrahydrofuran at -5 - 20℃; for 4h; Reagent/catalyst; Temperature;97.8%
With chloro-trimethyl-silane; potassium borohydride In tetrahydrofuran at 65℃; for 30h; Temperature; Reagent/catalyst; Inert atmosphere;97%
Stage #1: 4-(4-fluorophenyl)-6-isopropyl-2-(methanesulfonyl(methyl)amino)pyrimidine-5-carboxylic acid With potassium borohydride In tetrahydrofuran for 0.0833333h; Cooling with ice;
Stage #2: With aluminum (III) chloride In tetrahydrofuran at 74℃; for 4.08333h; Reagent/catalyst;		97.9%
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at -5 - 30℃; Reagent/catalyst; Temperature;96.4%
With sodium tetrahydroborate; chloro-trimethyl-silane In tetrahydrofuran for 24h; Reagent/catalyst; Reflux; Inert atmosphere;92%
methyl 4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methanesulfonyl)amino]pyrimidin-5-carboxylate

methyl 4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methanesulfonyl)amino]pyrimidin-5-carboxylate

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol for 4h;88.1%
ethyl 2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-carboxylic acid
147118-30-7

ethyl 2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-carboxylic acid

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Stage #1: ethyl 2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-carboxylic acid With diisobutylaluminium hydride In toluene at -78 - 0℃; Inert atmosphere;
Stage #2: With water In toluene		81%
With diisobutylaluminium hydride In toluene at -74℃; for 1h;277 mg
Multi-step reaction with 2 steps
1: lithium hydroxide monohydrate / water; methanol / 60 - 70 °C
2: lithium borohydride; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / -5 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: lithium hydroxide monohydrate; water / methanol / 60 - 70 °C
2: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / -5 - 30 °C
View Scheme
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

PhCH2CH2MgHal

PhCH2CH2MgHal

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 6 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
View Scheme
(E)-2-<(4-fluorophenyl)methylene>-4-methyl-3-oxopentanoic acid ethyl ester
122930-45-4

(E)-2-<(4-fluorophenyl)methylene>-4-methyl-3-oxopentanoic acid ethyl ester

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 5 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
View Scheme
ethyl 4-methyl-3-oxo-pentanoate
7152-15-0

ethyl 4-methyl-3-oxo-pentanoate

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 6 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
View Scheme
5-ethoxycarbonyl-6-(4'-fluorophenyl)-4-isopropyl-2-(methylamino)pyrimidine
147118-32-9

5-ethoxycarbonyl-6-(4'-fluorophenyl)-4-isopropyl-2-(methylamino)pyrimidine

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h
2: 277 mg / DIBAL-H / toluene / 1 h / -74 °C
View Scheme
ethyl 4-(4-fluorophenyl)-2-(methylsulfanyl)-6-(propan-2-yl)-pyrimidine-5-carboxylate
147118-27-2

ethyl 4-(4-fluorophenyl)-2-(methylsulfanyl)-6-(propan-2-yl)-pyrimidine-5-carboxylate

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 4 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
View Scheme
ethyl 4-(4-fluorophenyl)-6-isopropyl-2-(methylsulfonyl)pyrimidine-5-carboxylate
147118-28-3

ethyl 4-(4-fluorophenyl)-6-isopropyl-2-(methylsulfonyl)pyrimidine-5-carboxylate

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 3 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
View Scheme
N-(4-(4-fluorophenyl)-6-isopropyl-5-methylpyrimidin-2-yl)-N-methylmethanesulfonamide
953776-62-0

N-(4-(4-fluorophenyl)-6-isopropyl-5-methylpyrimidin-2-yl)-N-methylmethanesulfonamide

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / acetonitrile / 0.5 h / UV-irradiation; Inert atmosphere; Sealed flow reactor
2: sodium hydrogencarbonate; water / acetonitrile / 4 h / Reflux
View Scheme
Stage #1: N-(4-(4-fluorophenyl)-6-isopropyl-5-methylpyrimidin-2-yl)-N-methylmethanesulfonamide With N-Bromosuccinimide In acetonitrile at 20℃; for 4h; UV-irradiation;
Stage #2: With sodium hydrogencarbonate In acetonitrile for 4h; Reflux;
Stage #3: With water In acetonitrile at 20℃;
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / acetonitrile / 16 h / 20 °C / Inert atmosphere; UV-irradiation
2: water / tetrahydrofuran / 6 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / acetonitrile / 68 h / 20 °C / UV-irradiation
2: sodium hydrogencarbonate / acetonitrile / 4 h / Reflux
View Scheme
1-(4-Fluorophenyl)-3-isopropylpropan-1,3-dione
114433-94-2

1-(4-Fluorophenyl)-3-isopropylpropan-1,3-dione

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 5 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
View Scheme
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: water / tetrahydrofuran / 6 h / Reflux
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: water / tetrahydrofuran / 6 h / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate / acetone / 24 h / 20 °C
2.1: tetrahydrofuran / 0.17 h / 20 °C
2.2: 8 h / 40 °C
3.1: triethylamine / dichloromethane / 26 h / 0 - 20 °C
4.1: N-Bromosuccinimide / acetonitrile / 68 h / 20 °C / UV-irradiation
5.1: sodium hydrogencarbonate / acetonitrile / 4 h / Reflux
View Scheme
4-(4-fluorophenyl)-6-isopropyl-N,5-dimethylpyrimidin-2-amine
1207460-34-1

4-(4-fluorophenyl)-6-isopropyl-N,5-dimethylpyrimidin-2-amine

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 3 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
View Scheme
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: water / tetrahydrofuran / 6 h / Reflux
View Scheme
Multi-step reaction with 3 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
View Scheme
1-(4-fluorophenyl)-2-methyl-3-isopropylpropan-1,3-dione
1354455-77-8

1-(4-fluorophenyl)-2-methyl-3-isopropylpropan-1,3-dione

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 4 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
View Scheme
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: water / tetrahydrofuran / 6 h / Reflux
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: water / tetrahydrofuran / 6 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: tetrahydrofuran / 0.17 h / 20 °C
1.2: 8 h / 40 °C
2.1: triethylamine / dichloromethane / 26 h / 0 - 20 °C
3.1: N-Bromosuccinimide / acetonitrile / 68 h / 20 °C / UV-irradiation
4.1: sodium hydrogencarbonate / acetonitrile / 4 h / Reflux
View Scheme
N-(4-(4-fluorophenyl)-6-isopropyl-5-methylpyrimidin-2-yl)-N-methylmethanesulfonamide
953776-62-0

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
147118-36-3

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
147118-37-4

N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
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-[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
147118-36-3

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
147118-37-4

N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
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

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
147118-36-3

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
147118-37-4

N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
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

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
147118-36-3

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
147118-37-4

N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
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

1-(4-Fluorophenyl)-3-isopropylpropan-1,3-dione

A

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

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
147118-37-4

N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
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
4-methyl-3-oxopentanoic acid benzyl ester
94250-56-3

4-methyl-3-oxopentanoic acid benzyl ester

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: copper(l) chloride; sulfuric acid / methanol / 12 h / 50 °C
2.1: sodium nitrite; nitric acid / dichloromethane / 1 h / 0 °C
3.1: potassium carbonate; acetic acid butyl ester; p-toluenesulfonyl chloride / 2 h / 40 °C
3.2: 12 h / 120 °C
4.1: 5%-palladium/activated carbon; hydrogen / methanol / 5 h / 20 °C
5.1: sodium tetrahydroborate; chloro-trimethyl-silane / tetrahydrofuran / 24 h / Reflux; Inert atmosphere
View Scheme
benzyl 6-(4-fluorophenyl)-4-isopropyl-2-oxo-1,2,5,6-tetrahydropyrimidine-5-carboxylate

benzyl 6-(4-fluorophenyl)-4-isopropyl-2-oxo-1,2,5,6-tetrahydropyrimidine-5-carboxylate

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium nitrite; nitric acid / dichloromethane / 1 h / 0 °C
2.1: potassium carbonate; acetic acid butyl ester; p-toluenesulfonyl chloride / 2 h / 40 °C
2.2: 12 h / 120 °C
3.1: 5%-palladium/activated carbon; hydrogen / methanol / 5 h / 20 °C
4.1: sodium tetrahydroborate; chloro-trimethyl-silane / tetrahydrofuran / 24 h / Reflux; Inert atmosphere
View Scheme
benzyl 4-(4-fluorophenyl)-2-hydroxy-6-isopropylpyrimidine-5-carboxylate

benzyl 4-(4-fluorophenyl)-2-hydroxy-6-isopropylpyrimidine-5-carboxylate

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate; acetic acid butyl ester; p-toluenesulfonyl chloride / 2 h / 40 °C
1.2: 12 h / 120 °C
2.1: 5%-palladium/activated carbon; hydrogen / methanol / 5 h / 20 °C
3.1: sodium tetrahydroborate; chloro-trimethyl-silane / tetrahydrofuran / 24 h / Reflux; Inert atmosphere
View Scheme
benzyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidine-5-carboxylate

benzyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidine-5-carboxylate

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 5%-palladium/activated carbon; hydrogen / methanol / 5 h / 20 °C
2: sodium tetrahydroborate; chloro-trimethyl-silane / tetrahydrofuran / 24 h / Reflux; Inert atmosphere
View Scheme
Methyl 4-methyl-3-oxopentanoate
42558-54-3

Methyl 4-methyl-3-oxopentanoate

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 150 °C
2.1: copper(l) chloride; sulfuric acid / methanol / 12 h / 50 °C
3.1: sodium nitrite; nitric acid / dichloromethane / 1 h / 0 °C
4.1: potassium carbonate; acetic acid butyl ester; p-toluenesulfonyl chloride / 2 h / 40 °C
4.2: 12 h / 120 °C
5.1: 5%-palladium/activated carbon; hydrogen / methanol / 5 h / 20 °C
6.1: sodium tetrahydroborate; chloro-trimethyl-silane / tetrahydrofuran / 24 h / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: copper(l) chloride; sulfuric acid / methanol / 24 h / 80 °C / Inert atmosphere
2.1: copper dichloride; potassium carbonate; tert.-butylhydroperoxide / dichloromethane / 7 h / 40 °C
3.1: trichlorophosphate; N,N-dimethyl-aniline / 2.5 h / 80 °C / Inert atmosphere
4.1: sodium hydride / mineral oil; acetonitrile / 0.08 h
4.2: 7 h / Reflux
5.1: diisobutylaluminium hydride / toluene / 1.5 h / -15 - 0 °C
View Scheme
Multi-step reaction with 5 steps
1.1: copper(l) chloride; sulfuric acid / methanol / 24 h / 80 °C / Inert atmosphere
2.1: copper dichloride; potassium carbonate; tert.-butylhydroperoxide / dichloromethane / 7 h / 40 °C
3.1: trichlorophosphate; N,N-dimethyl-aniline / 2.5 h / 80 °C / Inert atmosphere
4.1: sodium hydride / mineral oil; acetonitrile / 0.08 h
4.2: 7 h / Reflux
5.1: diisobutylaluminium hydride / toluene / 1.5 h / -15 - 0 °C
View Scheme
Multi-step reaction with 5 steps
1.1: copper(l) chloride; sulfuric acid / methanol / 9 h / 78 °C
2.1: dipotassium peroxodisulfate / water / Reflux
3.1: potassium carbonate; p-toluenesulfonyl chloride / acetic acid butyl ester / 0.5 h / 45 °C
3.2: 3 h / 125 °C
4.1: sodium hydroxide / ethanol / 0.5 h / 82 °C
5.1: potassium borohydride / tetrahydrofuran / 0.08 h / Cooling with ice
5.2: 4.08 h / 74 °C
View Scheme
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: copper(l) chloride; sulfuric acid / methanol / 24 h / 80 °C / Inert atmosphere
2.1: copper dichloride; potassium carbonate; tert.-butylhydroperoxide / dichloromethane / 7 h / 40 °C
3.1: trichlorophosphate; N,N-dimethyl-aniline / 2.5 h / 80 °C / Inert atmosphere
4.1: sodium hydride / mineral oil; acetonitrile / 0.08 h
4.2: 7 h / Reflux
5.1: diisobutylaluminium hydride / toluene / 1.5 h / -15 - 0 °C
View Scheme
Multi-step reaction with 5 steps
1.1: copper(l) chloride; sulfuric acid / methanol / 24 h / 80 °C / Inert atmosphere
2.1: copper dichloride; potassium carbonate; tert.-butylhydroperoxide / dichloromethane / 7 h / 40 °C
3.1: trichlorophosphate; N,N-dimethyl-aniline / 2.5 h / 80 °C / Inert atmosphere
4.1: sodium hydride / mineral oil; acetonitrile / 0.08 h
4.2: 7 h / Reflux
5.1: diisobutylaluminium hydride / toluene / 1.5 h / -15 - 0 °C
View Scheme
Multi-step reaction with 5 steps
1.1: copper(l) chloride; sulfuric acid / methanol / 9 h / 78 °C
2.1: dipotassium peroxodisulfate / water / Reflux
3.1: potassium carbonate; p-toluenesulfonyl chloride / acetic acid butyl ester / 0.5 h / 45 °C
3.2: 3 h / 125 °C
4.1: sodium hydroxide / ethanol / 0.5 h / 82 °C
5.1: potassium borohydride / tetrahydrofuran / 0.08 h / Cooling with ice
5.2: 4.08 h / 74 °C
View Scheme
methyl 4-(4-fluorophenyl)-6-isopropyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

methyl 4-(4-fluorophenyl)-6-isopropyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: copper dichloride; potassium carbonate; tert.-butylhydroperoxide / dichloromethane / 7 h / 40 °C
2.1: trichlorophosphate; N,N-dimethyl-aniline / 2.5 h / 80 °C / Inert atmosphere
3.1: sodium hydride / mineral oil; acetonitrile / 0.08 h
3.2: 7 h / Reflux
4.1: diisobutylaluminium hydride / toluene / 1.5 h / -15 - 0 °C
View Scheme
Multi-step reaction with 4 steps
1.1: copper dichloride; potassium carbonate; tert.-butylhydroperoxide / dichloromethane / 7 h / 40 °C
2.1: trichlorophosphate; N,N-dimethyl-aniline / 2.5 h / 80 °C / Inert atmosphere
3.1: sodium hydride / mineral oil; acetonitrile / 0.08 h
3.2: 7 h / Reflux
4.1: diisobutylaluminium hydride / toluene / 1.5 h / -15 - 0 °C
View Scheme
Multi-step reaction with 4 steps
1.1: dipotassium peroxodisulfate / water / Reflux
2.1: potassium carbonate; p-toluenesulfonyl chloride / acetic acid butyl ester / 0.5 h / 45 °C
2.2: 3 h / 125 °C
3.1: sodium hydroxide / ethanol / 0.5 h / 82 °C
4.1: potassium borohydride / tetrahydrofuran / 0.08 h / Cooling with ice
4.2: 4.08 h / 74 °C
View Scheme
4-(4-fluorophenyl)-6-isopropyl-5-methoxycarbonyl-3,4-dihydropyrimidine-2(1H)-one

4-(4-fluorophenyl)-6-isopropyl-5-methoxycarbonyl-3,4-dihydropyrimidine-2(1H)-one

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: trichlorophosphate; N,N-dimethyl-aniline / 2.5 h / 80 °C / Inert atmosphere
2.1: sodium hydride / mineral oil; acetonitrile / 0.08 h
2.2: 7 h / Reflux
3.1: diisobutylaluminium hydride / toluene / 1.5 h / -15 - 0 °C
View Scheme
Multi-step reaction with 3 steps
1.1: trichlorophosphate; N,N-dimethyl-aniline / 2.5 h / 80 °C / Inert atmosphere
2.1: sodium hydride / mineral oil; acetonitrile / 0.08 h
2.2: 7 h / Reflux
3.1: diisobutylaluminium hydride / toluene / 1.5 h / -15 - 0 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate; p-toluenesulfonyl chloride / acetic acid butyl ester / 0.5 h / 45 °C
1.2: 3 h / 125 °C
2.1: sodium hydroxide / ethanol / 0.5 h / 82 °C
3.1: potassium borohydride / tetrahydrofuran / 0.08 h / Cooling with ice
3.2: 4.08 h / 74 °C
View Scheme
2-chloro-4-(4-fluoro-phenyl)-6-isopropyl-pyrimidine-5-carboxylic acid methyl ester
488798-38-5

2-chloro-4-(4-fluoro-phenyl)-6-isopropyl-pyrimidine-5-carboxylic acid methyl ester

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / mineral oil; acetonitrile / 0.08 h
1.2: 7 h / Reflux
2.1: diisobutylaluminium hydride / toluene / 1.5 h / -15 - 0 °C
View Scheme
N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
147118-36-3

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
147118-37-4

N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
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%
N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
147118-36-3

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

N-[5-(bromomethyl)-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
799842-07-2

N-[5-(bromomethyl)-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

Conditions
ConditionsYield
With phosphorus tribromide In toluene; acetonitrile at 10 - 20℃; for 1h; Inert atmosphere;99%
With phosphorus tribromide In dichloromethane at 0 - 10℃; for 1h;90.6%
With phosphorus tribromide In dichloromethane at 20℃; for 1h;82%
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)methyl formate

(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)methyl formate

Conditions
ConditionsYield
With fluorosulfonyl fluoride; caesium carbonate at 20℃; for 12h; Sealed tube;99%
triphenylsulfonium trifluoromethanesulfonate
66003-78-9

triphenylsulfonium trifluoromethanesulfonate

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

N-(4-(4-fluorophenyl)-6-isopropyl-5-(phenoxymethyl)pyrimidin-2-yl)-N-methylmethanesulfonamide

N-(4-(4-fluorophenyl)-6-isopropyl-5-(phenoxymethyl)pyrimidin-2-yl)-N-methylmethanesulfonamide

Conditions
ConditionsYield
With cesium hydroxide In 1,4-dioxane at 50℃; for 24h; Inert atmosphere; Glovebox;99%
triphenylphosphine
603-35-0

triphenylphosphine

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

[4-[4-fluorophenyl-6-(1-methylethyl)-2-[N-methyl-(N-methanesulfonyl)amino]]-5-pyrimidinyl]methylphenyltriphenylphosphonium bromide

[4-[4-fluorophenyl-6-(1-methylethyl)-2-[N-methyl-(N-methanesulfonyl)amino]]-5-pyrimidinyl]methylphenyltriphenylphosphonium bromide

Conditions
ConditionsYield
With hydrogen bromide In acetonitrile Solvent; Reflux;98%
triphenylphosphonium tetrafluoroborate

triphenylphosphonium tetrafluoroborate

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

((4-p-fluorophenyl-6-isopropyl-2-(N-methylmethylsulfonylamino)-5-pyrimidyl)methyl)triphenylphosphonium tetrafluoroborate

((4-p-fluorophenyl-6-isopropyl-2-(N-methylmethylsulfonylamino)-5-pyrimidyl)methyl)triphenylphosphonium tetrafluoroborate

Conditions
ConditionsYield
In acetonitrile for 24h; Reflux;97%
ethyl 5-(bromomethyl)-1,3-diphenyl-1H-pyrazole-4-carboxylate
191419-22-4

ethyl 5-(bromomethyl)-1,3-diphenyl-1H-pyrazole-4-carboxylate

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

ethyl 5-(((4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)methoxy)methyl)-1,3-diphenyl-1H-pyrazole-4-carboxylate

ethyl 5-(((4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)methoxy)methyl)-1,3-diphenyl-1H-pyrazole-4-carboxylate

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium hydroxide In tetrahydrofuran at 20℃;95%
triphenylphosphine hydrobromide
6399-81-1

triphenylphosphine hydrobromide

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

[4-[4-fluorophenyl-6-(1-methylethyl)-2-[N-methyl-(N-methanesulfonyl)amino]]-5-pyrimidinyl]methylphenyltriphenylphosphonium bromide

[4-[4-fluorophenyl-6-(1-methylethyl)-2-[N-methyl-(N-methanesulfonyl)amino]]-5-pyrimidinyl]methylphenyltriphenylphosphonium bromide

Conditions
ConditionsYield
In toluene for 10h; Reflux;94%
In toluene for 10h; Reflux;83%
silver(I) trifluoromethanethiolate
811-68-7

silver(I) trifluoromethanethiolate

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

N-(4-(4-fluorophenyl)-6-isopropyl-5-(((trifluoromethyl)thio)methyl)pyrimidin-2-yl)-N-methylmethanesulfonamide

N-(4-(4-fluorophenyl)-6-isopropyl-5-(((trifluoromethyl)thio)methyl)pyrimidin-2-yl)-N-methylmethanesulfonamide

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide In toluene at 80℃; for 10h; Schlenk technique; Inert atmosphere;93%
tributylphosphine
998-40-3

tributylphosphine

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

((4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethyl-sulfonamido)pyrimidin-5-yl)methyl)tributylphosphonium 2,2,2-trifluoro-acetate

((4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethyl-sulfonamido)pyrimidin-5-yl)methyl)tributylphosphonium 2,2,2-trifluoro-acetate

Conditions
ConditionsYield
Stage #1: trifluoroacetic anhydride; N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide With triethylamine In acetic acid butyl ester at 20 - 60℃;
Stage #2: tributylphosphine In acetic acid butyl ester for 2h; Product distribution / selectivity; Heating / reflux;		90%
...Expand
N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
147118-36-3

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

N-[5-chloromethyl-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide
925422-06-6

N-[5-chloromethyl-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide

Conditions
ConditionsYield
With methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 25℃; for 5h;88%
Ag(1+)*CF3S(1-)*(x)C2H3N

Ag(1+)*CF3S(1-)*(x)C2H3N

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

N-(4-(4-fluorophenyl)-6-isopropyl-5-(((trifluoromethyl)thio)methyl)pyrimidin-2-yl)-N-methylmethanesulfonamide

N-(4-(4-fluorophenyl)-6-isopropyl-5-(((trifluoromethyl)thio)methyl)pyrimidin-2-yl)-N-methylmethanesulfonamide

Conditions
ConditionsYield
With 1,2-Diiodoethane; tetra-(n-butyl)ammonium iodide; triphenylphosphine In N,N-dimethyl-formamide; acetonitrile at 80℃; for 0.25h; Inert atmosphere; Sealed tube;87%
tetramethylammonium trifluoromethylselenate(0)
75264-92-5

tetramethylammonium trifluoromethylselenate(0)

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

N-(4-(4-fluorophenyl)-6-isopropyl-5-(((trifluoromethyl)selanyl)methyl)pyrimidin-2-yl)-N-methylmethanesulfonamide

N-(4-(4-fluorophenyl)-6-isopropyl-5-(((trifluoromethyl)selanyl)methyl)pyrimidin-2-yl)-N-methylmethanesulfonamide

Conditions
ConditionsYield
With calcium chloride In acetonitrile at 80℃; for 2h; Time; Inert atmosphere; Sealed tube; Glovebox;87%
diphenylphosphinous acid methyl ester
4020-99-9

diphenylphosphinous acid methyl ester

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

N-(5-((diphenylphosphoryl)methyl)-4-(4-fluorophenyl)- 6-isopropylpyrimidin-2-yl)-N-methylmethansulfonamide
289042-10-0

N-(5-((diphenylphosphoryl)methyl)-4-(4-fluorophenyl)- 6-isopropylpyrimidin-2-yl)-N-methylmethansulfonamide

Conditions
ConditionsYield
Stage #1: N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide With phosphorus tribromide In acetonitrile at 20℃;
Stage #2: diphenylphosphinous acid methyl ester at 60℃;		86%
N-[5-(bromomethyl)-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
799842-07-2

N-[5-(bromomethyl)-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

C32H38F2N6O5S2

C32H38F2N6O5S2

Conditions
ConditionsYield
With potassium carbonate In toluene for 12h; Reflux;82.4%
sodium phenoxide
139-02-6

sodium phenoxide

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

N-(4-(4-fluorophenyl)-6-isopropyl-5-(phenoxymethyl)pyrimidin-2-yl)-N-methylmethanesulfonamide

N-(4-(4-fluorophenyl)-6-isopropyl-5-(phenoxymethyl)pyrimidin-2-yl)-N-methylmethanesulfonamide

Conditions
ConditionsYield
Stage #1: N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide With 1,2-Diiodoethane; N,N-dimethyl-formamide; triphenylphosphine at 20℃; for 0.0166667h; Sealed tube; Inert atmosphere;
Stage #2: sodium phenoxide at 20℃; Sealed tube; Inert atmosphere;		77%
(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

N-(4-(4-fluorophenyl)-6-isopropyl-5-((trifluoromethoxy)methyl)pyrimidin-2-yl)-N-methylmethanesulfonamide

N-(4-(4-fluorophenyl)-6-isopropyl-5-((trifluoromethoxy)methyl)pyrimidin-2-yl)-N-methylmethanesulfonamide

Conditions
ConditionsYield
With potassium fluoride; 2-fluoropyridine; silver trifluoromethanesulfonate; Selectfluor In ethyl acetate at 20℃; for 12h; Glovebox; Inert atmosphere;76%
trimethyl(pentafluoroethyl)silane
124898-13-1

trimethyl(pentafluoroethyl)silane

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

N-(4-(4-fluorophenyl)-6-isopropyl-5-((perfluoroethoxy)methyl)pyrimidin-2-yl)-N-methylmethanesulfonamide

N-(4-(4-fluorophenyl)-6-isopropyl-5-((perfluoroethoxy)methyl)pyrimidin-2-yl)-N-methylmethanesulfonamide

Conditions
ConditionsYield
With potassium fluoride; 2-fluoropyridine; silver trifluoromethanesulfonate; lithium trifluoromethanesulfonate; Selectfluor In ethyl acetate at 20℃; for 12h; Inert atmosphere;64%
N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
147118-36-3

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

N-(5-(fluoromethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide

N-(5-(fluoromethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide

Conditions
ConditionsYield
With potassium 2-(difluoro(trifluoromethoxy)methoxy)-2,2-difluoroacetate; tetramethylammonium fluoride at 150℃; for 5h; Glovebox; Inert atmosphere; Schlenk technique; Sealed tube;57%
N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide
147118-36-3

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

[4-(4-fluorophenyl)-2-methylamino-6-(1-methylethyl)-pyrimidin-5-yl]methanol

[4-(4-fluorophenyl)-2-methylamino-6-(1-methylethyl)-pyrimidin-5-yl]methanol

Conditions
ConditionsYield
With acetone; lithium diisopropyl amide In tetrahydrofuran at -10℃; for 4.5h; Temperature;49.6%
acetone
67-64-1

acetone

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

N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide

[4-(4-fluorophenyl)-2-[(2-hydroxy-2-methylpropyl)sulfonyl(methyl)amino]-6-(1-methylethyl)-pyrimidin-5-yl]methanol

[4-(4-fluorophenyl)-2-[(2-hydroxy-2-methylpropyl)sulfonyl(methyl)amino]-6-(1-methylethyl)-pyrimidin-5-yl]methanol

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -10℃; for 4.5h; Temperature;49.6%

4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-n-methylsulfonyl)amino]pyrimidine-5-yl-methanol Chemical Properties

Molecular structure of 4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-n-methylsulfonyl)amino]pyrimidine-5-yl-methanol (CAS NO.147118-36-3) is:

Product Name: 4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-n-methylsulfonyl)amino]pyrimidine-5-yl-methanol
CAS Registry Number: 147118-36-3
Molecular Formula: C16H20FN3O3S
Molecular Weight: 353.41 
Index of Refraction: 1.579
Molar Refractivity: 89.145 cm3
Molar Volume: 268.288 cm3
Surface Tension: 54.768 dyne/cm
Density: 1.317 g/cm3
Flash Point: 279.338 °C
Enthalpy of Vaporization: 85.82 kJ/mol
Boiling Point: 538.273 °C at 760 mmHg 
Product Categories: INTERMEDIATESOFROSUVASTATINCALCIUM;Rosuvastatin Calcium and its intermediates

4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-n-methylsulfonyl)amino]pyrimidine-5-yl-methanol Specification

 4-(4-Fluorophenyl)-6-isopropyl-2-[(N-methyl-n-methylsulfonyl)amino]pyrimidine-5-yl-methanol , its cas register number is 147118-36-3. It also can be called Methanesulfonamide,N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(1-methylethyl)-2-pyrimidinyl]-N-methyl- ; N-[4-(4-Fluorophenyl)-5-hydroxymethyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide .

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