Cesium carbonate → HCID 15950521, compound

HRID 271117Notes

Reaction equation

HRID 271117 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:3]=1.I[CH2:23][CH2:24][CH3:25].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O.CN(C=O)C>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:23][CH2:24][CH3:25])[CH:16]=2)([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 336431-IodopropaneHCID 15951419HCID 15951419, compound

Product 1

HCID 15950521HCID 15950521, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-amino-5-(3-hydroxyphenyl)-3-methyl-5-pyridin-4-yl-3,5-dihydro-4H-imidazol-4-one (0.13 g, 0.46 mmol) in acetone (20 mL) and DMF (1 mL) is added 1-iodopropane (0.07 mL, 0.69 mmol) and Cs2CO3 (1.50 g, 4.60 mmo). After refluxed for 1 hour, the solvent is evaporated and the crude material was purified by chromatography (silica gel, EtOAc/2M methanolic NH3: 97/3) to give the title compound (0.145 g, 97%) as a solid. mp: 173-175° C.; MS(+) ES: 325 (M+H)+.

Workup

  1. temperatureAfter refluxed for 1 hour
  2. customthe solvent is evaporated
  3. customthe crude material was purified by chromatography (silica gel, EtOAc/2M methanolic NH3: 97/3)

Sources & evidence

ORD record
ord-a4c1734597a9490c8c64eed5baad8da8
Source dataset
uspto-grants-2008_11
Patent number
US07452885B2

Reaction notes

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