Methyl iodide → HCID 53629128, compound

HRID 1924291Notes

Reaction equation

HRID 1924291 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:10]=2[CH2:11][N:12]2[CH2:16][CH:15]([CH2:17][CH2:18][CH3:19])[CH2:14][C:13]2=[O:20])[CH:7]=1.IC.[C:29]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:29][O:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:10]=2[CH2:11][N:12]2[CH2:16][CH:15]([CH2:17][CH2:18][CH3:19])[CH2:14][C:13]2=[O:20])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 53629173HCID 53629173, compound

Product 1

HCID 53629128HCID 53629128, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-[(6-hydroxy-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]-4-propylpyrrolidin-2-one x149 (1.71 mmol, 1 eq, 0.6 g) in acetone (100 ml) is added iodomethane (17.1 mmol, 10 eq, 1.065 ml) and K2CO3 (17.1 mmol, 10 eq, 2.36 g). The mixture is refluxed for 5 minutes. Solvent is evaporated under reduced pressure. The crude product is purified by chromatography on silicagel (AcOEt/hexane: 1/1) and recrystallized in AcOEt to afford 0.19 g of 1-[(6-methoxy-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]-4-propylpyrrolidin-2-one 204.

Workup

  1. temperatureThe mixture is refluxed for 5 minutes
  2. customSolvent is evaporated under reduced pressure
  3. customThe crude product is purified by chromatography on silicagel (AcOEt/hexane: 1/1)
  4. customrecrystallized in AcOEt

Sources & evidence

ORD record
ord-7c288378c2394614a4f7ad979657e7d2
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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