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Lithium Hydroxide → 4-(4-tert-Butoxycarbonylamino-phenylsulfanyl)-3-(7-tert-butyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid

HRID 605359
Notes
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Reaction equation

HRID 605359 reaction equation
C[O:2][C:3](=[O:40])[C:4]1[CH:9]=[CH:8][C:7]([S: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]([C:36]([CH3:39])([CH3:38])[CH3:37])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)[CH:5]=1.[Li+].[OH-]>C1COCC1.CO>[C:21]([O:20][C:18]([NH:17][C:14]1[CH:13]=[CH:12][C:11]([S:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:40])=[O:2])=[CH:5][C:6]=2[NH:25][C:26]2[C:27]3[CH:35]=[CH:34][C:33]([C:36]([CH3:39])([CH3:38])[CH3:37])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)=[CH:16][CH:15]=1)=[O:19])([CH3:24])([CH3:23])[CH3:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 670407204-(4-tert-Butoxycarbonylamino-phenylsulfanyl)-3-(7-tert-butyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid methyl ester

Product 1

HCID 670405944-(4-tert-Butoxycarbonylamino-phenylsulfanyl)-3-(7-tert-butyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acidYield 971.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(4-tert-butoxycarbonylamino-phenylsulfanyl)-3-(7-tert-butyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid methyl ester (0.53 g, 0.1 mmol) in a mixture of THF (9 mL) and MeOH (3 mL) was added aqueous LiOH [prepared from LiOH monohydrate (0.21 g, 5.0 mmol) and H2O (3 mL)] dropwise at room temperature. The mixture was stirred at 50° C. for 4 hours, and then evaporated. The aqueous mixture was diluted with H2O, washed with AcOEt, and then carefully acidified to pH 4-5 with 10% HCl at 5° C. under stirring. The resulting solid was collected by filtration, washed with H2O, and dried at 60° C. overnight under reduced pressure to give the title compound as yellow powder (0.53 g, 99%).

Workup

  1. customevaporated
  2. additionThe aqueous mixture was diluted with H2O
  3. washwashed with AcOEt
  4. customcarefully acidified to pH 4-5 with 10% HCl at 5° C.
  5. stirringunder stirring
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with H2O
  8. customdried at 60° C. overnight under reduced pressure

Sources & evidence

ORD record
ord-746f9cafb0b6496ab3c8ed9926e968ef
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07910595B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes