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

HRID 1091824Notes

Reaction equation

HRID 1091824 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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

Workup

  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%)

Sources & evidence

ORD record
ord-d3bc4d9a208f4c24b398424854fd084d
Source dataset
uspto-grants-2012_03
Patent number
US08129399B2

Reaction notes

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