benzyl 2-chloro-4-[5-chloro-4-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yloxy)-pyrimidin-2-ylamino]-5-methoxy-benzoate → 2-chloro-4-[5-chloro-4-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yloxy)-pyrimidin-2-ylamino]-5-methoxy-benzoic acid

HRID 81356Notes

Reaction equation

HRID 81356 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([NH:18][C:19]2[N:24]=[C:23]([O:25][C:26]3[CH:34]=[CH:33][CH:32]=[C:31]4[C:27]=3[C:28](=[O:36])[N:29]([CH3:35])[CH2:30]4)[C:22]([Cl:37])=[CH:21][N:20]=2)[C:15]([O:38][CH3:39])=[CH:14][C:3]=1[C:4]([O:6]CC1C=CC=CC=1)=[O:5]>C1COCC1.C(#N)C.[OH-].[OH-].[Pd+2]>[Cl:1][C:2]1[CH:17]=[C:16]([NH:18][C:19]2[N:24]=[C:23]([O:25][C:26]3[CH:34]=[CH:33][CH:32]=[C:31]4[C:27]=3[C:28](=[O:36])[N:29]([CH3:35])[CH2:30]4)[C:22]([Cl:37])=[CH:21][N:20]=2)[C:15]([O:38][CH3:39])=[CH:14][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 1

HCID 58522534benzyl 2-chloro-4-[5-chloro-4-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yloxy)-pyrimidin-2-ylamino]-5-methoxy-benzoate

Product 1

HCID 585226292-chloro-4-[5-chloro-4-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yloxy)-pyrimidin-2-ylamino]-5-methoxy-benzoic acid

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzyl 2-chloro-4-[5-chloro-4-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yloxy)-pyrimidin-2-ylamino]-5-methoxy-benzoate (75 mg) is dissolved in THF (150 mL), Pd(OH)2 (0.01 g) is added and the mixture is stirred for 2 h under H2 gas. For working up the mixture is diluted with ACN (20 mL) and Isolute is added. The solvent is filtered off from the catalyst and the solvent is eliminated in vacuo.

Workup

  1. additionis added
  2. filtrationThe solvent is filtered off from the catalyst

Sources & evidence

ORD record
ord-7583c66c6d484ecca2e2808a2873b164
Source dataset
uspto-grants-2014_09
Patent number
US08846689B2

Reaction notes

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