Potassium Carbonate → 4-(4-isopropyl-phenyl)-1-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-benzyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

HRID 445171Notes

Reaction equation

HRID 445171 reaction equation
[OH:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][C:17]#[CH:18])=[CH:12][CH:13]=2)[C:8]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=2)=[N:7][C:6]1=[O:28].C(=O)([O-])[O-].[K+].[K+].[CH3:39][O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH2:47][CH2:48]CS([O-])(=O)=O>CC(C)=O>[CH:25]([C:22]1[CH:21]=[CH:20][C:19]([C:8]2[C:9]3[C:14](=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]#[CH:18])[CH:10]=3)[N:5]([CH2:4][C:3]3[CH:29]=[CH:30][CH:31]=[CH:32][C:2]=3[O:1][CH2:48][CH2:47][O:46][CH2:45][CH2:44][O:43][CH2:42][CH2:41][O:40][CH3:39])[C:6](=[O:28])[N:7]=2)=[CH:24][CH:23]=1)([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 102241931-(2-hydroxy-benzyl)-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-oneHCID 865942852-[2-(2-Methoxy-ethoxy)-ethoxy]-ethyl-methanesulfonate

Product 1

HCID 103034284-(4-isopropyl-phenyl)-1-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-benzyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 125 mg (0.29 mmol) of 1-(2-hydroxy-benzyl)-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one in acetone (5 ml) is added potassium carbonate (407 mg, 2.94 mmol) followed by 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl-methanesulfonate (as prepared in Step A, Example RT-5) (357 mg, 1.47 mmol). The reaction mixture is heated at reflux overnight. After cooling to room temperature, the reaction mixture is quenched with water and extracted with EtOAc (2×20 ml). The combined organic layers are washed with brine, dried (Na2SO4), filtered and evaporated in vacuo to provide a yellow oil which is purified by preparative TLC chromatography on Silica gel using dichloromethane/ether (1:1) to provide the title compound as a yellow oil. Yield: 29 mg (17%).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux overnight
  3. customthe reaction mixture is quenched with water
  4. extractionextracted with EtOAc (2×20 ml)
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto provide a yellow oil which
  10. customis purified by preparative TLC chromatography on Silica gel

Sources & evidence

ORD record
ord-f962e140ad1343959eb91980991a5c77
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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