Potassium Carbonate → HCID 178441858, compound

HRID 1974924Notes

Reaction equation

HRID 1974924 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([CH2:16]CBr)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-:20].[K+].[K+]>CS(C)=O.O>[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([CH2:16][OH:20])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 178441837HCID 178441837, compound

Product 1

HCID 178441858HCID 178441858, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a suspension of 2.0 g of impure 2-butyl-6-(bromethyl)-4(1H)-quinazolinone (from Example 3) in 35 ml of dimethylsulfoxide and 20 ml of water is added 1.0 g of potassium carbonate. The reaction mixture is heated at reflux for 6 hours, resulting in a complete solution. Upon cooling slowly to room temperature a white precipitate forms and is collected by filtration. The filter cake is purified by flash chromatography on silica gel, eluting with 9:1 chloroform-methanol to give 0.67 g of the desired product as a white solid. CI MASS SPEC 233(MH+).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 6 hours
  3. customresulting in a complete solution
  4. filtrationis collected by filtration
  5. customThe filter cake is purified by flash chromatography on silica gel
  6. washeluting with 9:1 chloroform-methanol

Sources & evidence

ORD record
ord-18fedbe4fda342dd9508d6d309774f2a
Source dataset
uspto-grants-1994_02
Patent number
US05284852

Reaction notes

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