Water → HCID 22174885, compound

HRID 1410394Notes

Reaction equation

HRID 1410394 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[C:13]([CH3:14])=[N:12][N:11]([C:15]3[N:20]=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[CH:18]=[CH:17][N:16]=3)[C:10]2=[O:27])=[CH:4][CH:3]=1.[C:28](=O)([O-])[O-].[K+].[K+].IC.O>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:13]([CH3:14])=[N:12][N:11]([C:15]3[N:20]=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[CH:18]=[CH:17][N:16]=3)[C:10]=2[O:27][CH3:28])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22174881HCID 22174881, compound

Product 1

HCID 22174885HCID 22174885, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-(4-chloro-phenylsulfanyl)-5-methyl-2(4-pyridin-2yl-pyrimidin-2-yl)-2,4-dihydro-pyrazol-3-one (0.344 g, 0.869 mmol) in acetone (10 mL) was added potassium carbonate (ca. 3 g) and iodomethane (0.130 g, 0.912 mmol). The suspension was heated to reflux and stirred for 2 hours. The suspension was allowed to cool to room temperature, and water (100 mL) was added. The mixture was extracted with diethyl ether (50 mL), and the organic phase was washed with brine (50 mL), dried (magnesium sulfate), filtered and concentrated to afford a white solid. Flash chromatography over silica (methylene chloride/2M ammonia in methanol, two columns) provided 0.007 g (2%) of the product as a white solid. 1H NMR analysis was consistent with the assigned structure.

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux
  3. extractionThe mixture was extracted with diethyl ether (50 mL)
  4. washthe organic phase was washed with brine (50 mL)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a white solid

Sources & evidence

ORD record
ord-9bc0c1eaed93431b969750c4bcbb0f37
Source dataset
uspto-grants-2014_12
Patent number
US08921547B2

Reaction notes

Loading…