Potassium Carbonate → 6-(3-cyclopropyl-3-fluoroazetidin-1-yl)-N-(3-methyl-1H-pyrazol-5-yl)-2-(methylsulfonyl)pyrimidin-4-amine

HRID 499093

Reaktionsgleichung

Reaktionsgleichung von HRID 499093
[CH:1]1([C:4]2([F:23])[CH2:7][N:6]([C:8]3[N:13]=[C:12](SC)[N:11]=[C:10]([NH:16][C:17]4[NH:21][N:20]=[C:19]([CH3:22])[CH:18]=4)[CH:9]=3)[CH2:5]2)[CH2:3][CH2:2]1.O[O:25][S:26]([O-:28])=O.[K+].OS([O-])=O.[Na+].[C:35]([O-])([O-])=O.[K+].[K+]>CO.O>[CH:1]1([C:4]2([F:23])[CH2:7][N:6]([C:8]3[N:13]=[C:12]([S:26]([CH3:35])(=[O:28])=[O:25])[N:11]=[C:10]([NH:16][C:17]4[NH:21][N:20]=[C:19]([CH3:22])[CH:18]=4)[CH:9]=3)[CH2:5]2)[CH2:2][CH2:3]1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 23665763Sodium BisulfiteHCID 23707502Potassium hydroxy sulfiteHCID 178503490HCID 178503490, Verbindung

Produkt 1

HCID 1784282456-(3-cyclopropyl-3-fluoroazetidin-1-yl)-N-(3-methyl-1H-pyrazol-5-yl)-2-(methylsulfonyl)pyrimidin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 6-(3-cyclopropyl-3-fluoroazetidin-1-yl)-N-(3-methyl-1H-pyrazol-5-yl)-2-(methylthio)pyrimidin-4-amine (130 g, 389 mmol) in MeOH (5.2 L) was cooled to 0° C. A solution of oxone (526 g, 855 mmol) in H2O (5.2 L) was slowly added to the slurry keeping the temperature below 5° C. After addition the reaction was allowed to warm to room temperature overnight. A 10% solution of NaHSO3 (325 ml) and a 10% solution of K2CO3 (2.6 L) was then added to neutralize the reaction mixture, the solution filtered and the filter cake washed with H2O (3.3 L). The solid was slurried in H2O (2.6 L), the solution filtered and the filter cake washed with H2O (3.3 L). The solid was dried under vacuum (72.3 g, 51%). 1H NMR (DMSO): 0.47 (2H, m), 0.60 (2H, m), 1.43-1.46 (1H, m), 2.20 (3H, s), 3.25 (3H, s), 3.97-4.11 (4H, m), 5.93 (1H, br s), 6.47 (1H, br s), 9.88 (1H, s), 12.01 (1H, br s). ES+ 367

Aufarbeitung

  1. customthe temperature below 5° C
  2. additionAfter addition the reaction
  3. filtrationthe solution filtered
  4. washthe filter cake washed with H2O (3.3 L)
  5. filtrationthe solution filtered
  6. washthe filter cake washed with H2O (3.3 L)
  7. customThe solid was dried under vacuum (72.3 g, 51%)

Quellen und Nachweise

ORD-Eintrag
ord-55052ea5a74f40d09cabf1409060c720
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767672B2

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