Lithium Hydroxide → 2-Fluoro-4-[6-(1-trityl-1H-pyrazol-4-yl)-quinazolin-4-yl]benzoic acid

HRID 1792610Notes

Reaction equation

HRID 1792610 reaction equation
[F:1][C:2]1[CH:12]=[C:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]4[CH:24]=[N:25][N:26]([C:28]([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH:27]=4)[CH:21]=3)[N:16]=[CH:15][N:14]=2)[CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[OH-].[Li+]>C(O)C.O>[F:1][C:2]1[CH:12]=[C:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]4[CH:24]=[N:25][N:26]([C:28]([C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)([C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=5)[C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)[CH:27]=4)[CH:21]=3)[N:16]=[CH:15][N:14]=2)[CH:10]=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 22031192Ethyl 2-fluoro-4-[6-(1-trityl-1H-pyrazol-4-yl)-quinazolin-4-yl]benzoate

Product 1

HCID 220314572-Fluoro-4-[6-(1-trityl-1H-pyrazol-4-yl)-quinazolin-4-yl]benzoic acidYield 72.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

0.82 g ethyl 2-fluoro-4-[6-(1-trityl-1H-pyrazol-4-yl)-quinazolin-4-yl]benzoate (compound in Example 752) was dissolved in 30 mL solvent mixture of ethanol and water (2:1), then 0.11 g lithium hydroxide was added thereto, and the mixture was heated for 5 hours under reflux. The reaction solution was neutralized under ice-cooling. The solution was extracted with dichloromethane and recrystallized from ethanol/ether, to give 570 mg of the title compound as pale yellow crystals.

Workup

  1. temperaturethe mixture was heated for 5 hours
  2. temperatureunder reflux
  3. temperaturecooling
  4. extractionThe solution was extracted with dichloromethane
  5. customrecrystallized from ethanol/ether

Sources & evidence

ORD record
ord-3f764503dee34429909b92035f5fc42b
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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