Lithium Hydroxide → 3-(6-(4-Phenoxyphenylamino)pyrimidin-4-ylamino)benzoic acid

HRID 1053228Notes

Reaction equation

HRID 1053228 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[N:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]3[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=3)[C:25]([O:27]C)=[O:26])[CH:16]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>CO.C1COCC1.O>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]2[N:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]3[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=3)[C:25]([OH:27])=[O:26])[CH:16]=2)=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57708324Methyl 3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)benzoate

Product 1

HCID 577083343-(6-(4-Phenoxyphenylamino)pyrimidin-4-ylamino)benzoic acidYield 69.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)benzoate (0.3 g, 0.72 mmol) in methanol/THF (2/2, 4 mL) was added LiOH (0.122 g, 2.9 mmol) in H2O (4 mL) and the reaction mixture was stirred at rt for 2 h. It was concentrated under reduced pressure. the residue was diluted with water (2 mL) and was extracted with dichloromethane (5 mL). The aqueous layer was separated and was acidified with 1.5 N HCl (pH ˜5-6) to get a white precipitate, which was collected by filtration and dried under vacuum to give 3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)benzoic acid (0.2 g 69%) as a white solid.

Workup

  1. concentrationIt was concentrated under reduced pressure
  2. additionthe residue was diluted with water (2 mL)
  3. extractionwas extracted with dichloromethane (5 mL)
  4. customThe aqueous layer was separated
  5. customto get a white precipitate, which
  6. filtrationwas collected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-951fec5d829d4f69a0e6ed5f39fe6d6e
Source dataset
uspto-grants-2016_07
Patent number
US09393246B2

Reaction notes

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