Toluene → Methyl 4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinecarboxylate

HRID 1160660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160660
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH:18]([CH3:20])[CH3:19])[N:11]=[C:10](OS(C3C=CC(C)=CC=3)(=O)=O)[N:9]=2)=[CH:4][CH:3]=1.[CH3:32][NH:33][S:34]([CH3:37])(=[O:36])=[O:35].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH:18]([CH3:20])[CH3:19])[N:11]=[C:10]([N:33]([CH3:32])[S:34]([CH3:37])(=[O:36])=[O:35])[N:9]=2)=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 97632N-MethylmethanesulfonamideHCID 17989602Rosuvastatin Impurity 1622×

Produkt 1

HCID 9929821Methyl 4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinecarboxylateAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

In a 50 mL-volume glass flask equipped with a stirrer, a thermometer and a reflux condenser were placed 1.1 g (2.5 mmol.) of 4-(4-fluorophenyl)-6-isopropyl-5-methoxycarbonyl-2-(p-toluenesulfonyloxy)pyrimidine, 0.55 g (5.0 mmol.) of N-methylmethanesulfonamide, 0.69 g (5.0 mmol.) of potassium carbonate (available from Wako Junyaku Co., Ltd., special grade), 0.32 g (1.0 mmol.) of tetrabutylammonium bromide, 20 mL of toluene and 5 mL of water. The mixture was heated to 85° C. for 28 hours under refluxing, to carry out reaction. After the reaction was complete, the reaction mixture was cooled to room temperature. To the reaction mixture were added 10 mL of water and 7 mL of acetone, and the organic liquid portion was separated. The organic liquid portion was analyzed by high performance liquid chromatography. It was confirmed that 0.6 g of 4-(4-fluorophenyl)-6-isopropyl-5-methoxycarbonyl-2-(N-methyl-N-methanesulfonylamino)pyrimidine was produced. The yield was 63% (based on the amount of 4-(4-fluorophenyl)-6-isopropyl-5-methoxycarbonyl-2-(p-toluenesulfonyloxy)pyrimidine).

Aufarbeitung

  1. customIn a 50 mL-volume glass flask equipped with a stirrer
  2. temperatureunder refluxing
  3. customreaction
  4. temperaturethe reaction mixture was cooled to room temperature
  5. customthe organic liquid portion was separated
  6. customwas produced

Quellen und Nachweise

ORD-Eintrag
ord-b13507b8ac1d4cafae3b43c3152a2093
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816528B2

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