Lithium Hydroxide → 7-(2-Fluoro-4-iodophenylamino)-8-fluoro-4-methylquinazoline-6-carboxylic acid

HRID 558248Notes

Reaction equation

HRID 558248 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:19]([F:20])=[C:18]2[C:13]([C:14]([CH3:21])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[C:22]([O:24]C)=[O:23].[Li+].[OH-]>C1COCC1.O>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:19]([F:20])=[C:18]2[C:13]([C:14]([CH3:21])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[C:22]([OH:24])=[O:23]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59519426Methyl 7-(2-fluoro-4-iodophenylamino)-8-fluoro-4-methylquinazoline-6-carboxylate

Product 1

HCID 595194867-(2-Fluoro-4-iodophenylamino)-8-fluoro-4-methylquinazoline-6-carboxylic acidYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 7-(2-fluoro-4-iodophenylamino)-8-fluoro-4-methylquinazoline-6-carboxylate (205 mg, 0.48 mmol) in a mixture of THF (10 ml) and H2O (5 ml) was added a solution of LiOH (57 mg, 2.4 mmol) in H2O (2.4 ml). After stirring at room temperature for 4 h, the reaction was concentrated, acidified with 1 M. HCl solution, and extracted with EtOAc (2×20 ml). The organic solution was dried over MgSO4 and concentrated to give 190 mg (96%) the title compound as an orange solid.

Workup

  1. concentrationthe reaction was concentrated
  2. extractionHCl solution, and extracted with EtOAc (2×20 ml)
  3. dry with materialThe organic solution was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-91c5d8da5f774444be05b771d6512848
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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