Acetone → HCID 10144601, compound

HRID 445168Notes

Reaction equation

HRID 445168 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]#[CH:19])=[CH:13][CH:14]=2)[C:9]([C:20]2[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=2)=[N:8][C:7]1=[O:29].[C:33](=[O:36])([O-])[O-].[K+].[K+].S([O-])(=O)(=O)C.C[C:45]([CH3:47])=[O:46]>>[CH:26]([C:23]1[CH:24]=[CH:25][C:20]([C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]#[CH:19])[CH:11]=3)[N:6]([CH2:5][C:4]3[CH:30]=[CH:31][CH:32]=[C:2]([O:1][CH2:11][CH2:12][O:16][CH2:17][CH2:18][O:46][CH2:45][CH2:47][O:36][CH3:33])[CH:3]=3)[C:7](=[O:29])[N:8]=2)=[CH:21][CH:22]=1)([CH3:27])[CH3:28]

Participants

5

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 85257MethanesulfonateHCID 10273916HCID 10273916, compound

Product 1

HCID 10144601HCID 10144601, compound

Procedure

To a solution of 100 mg (0.236 mmol) of 1-(3-hydroxy-benzyl)-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one in acetone (5 ml) is added potassium carbonate (326 mg, 2.36 mmol) followed by the mesylate prepared in Step A (5 ml, 1.18 mmol). The reaction mixture is heated at reflux for 2 days. 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 flash chromatography on silica gel using dichloromethane/t-butyl methyl ether (1:1) to provide the title compound as a yellow oil. Yield: 101 mg (75%).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 2 days
  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 flash chromatography on silica gel

Sources & evidence

ORD record
ord-4d1f6fe401cc4f2ea15fe365468149e8
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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