Lithium Hydroxide → HCID 67040533, compound

HRID 605354Notes

Reaction equation

HRID 605354 reaction equation
C[O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:13][CH:12]=2)=[C:6]([NH:25][C:26]2[C:27]3[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)[CH:5]=1.[Li+].[OH-]>C1COCC1>[C:21]([O:20][C:18]([NH:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:39])=[O:2])=[CH:5][C:6]=2[NH:25][C:26]2[C:27]3[CH:35]=[CH:34][C:33]([CH:36]([CH3:37])[CH3:38])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)=[CH:12][CH:13]=1)=[O:19])([CH3:23])([CH3:22])[CH3:24]

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 67040882HCID 67040882, compound

Product 1

HCID 67040533HCID 67040533, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-(4-tert-butoxycarbonylamino-phenoxy)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid methyl ester (4.30 g, 8.1 mmol) in THF (43 mL) was added aqueous LiOH [prepared from LiOH monohydrate (1.08 g) and H2O (11 mL)] dropwise at room temperature. The mixture was stirred at room temperature for 21 hours. Additional aqueous LiOH [prepared from LiOH monohydrate (0.70 g) and H2O (7 mL)] was added at room temperature. The mixture was mixture was stirred at 35° C. for 6 hours, and then evaporated. The aqueous mixture was diluted with 150 mL of H2O, washed with AcOEt, and treated with active charcoal. The mixture was filtered and the filtrate was carefully acidified to pH 4-5 with 1N HCl under stirring. The resulting solid was collected by filtration, washed with H2O, and dried at 40° C. for 1 day under reduced pressure to give the title compound as pale yellow crystal (4.06 g, 97%).

Workup

  1. stirringwas stirred at 35° C. for 6 hours
  2. customevaporated
  3. additionThe aqueous mixture was diluted with 150 mL of H2O
  4. washwashed with AcOEt
  5. additiontreated with active charcoal
  6. filtrationThe mixture was filtered
  7. stirringunder stirring
  8. filtrationThe resulting solid was collected by filtration
  9. washwashed with H2O
  10. customdried at 40° C. for 1 day under reduced pressure

Sources & evidence

ORD record
ord-6850f9993ede41db92824b49ec7ac4cf
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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