Sodium Hydroxide → 2-(2-(2-Chlorophenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acid

HRID 42061Notes

Reaction equation

HRID 42061 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[CH:12][C:11]([NH:14][C:15]2[CH:24]=[CH:23][C:22]([CH:25]3[CH2:27][CH2:26]3)=[CH:21][C:16]=2[C:17]([O:19]C)=[O:18])=[CH:10][N:9]=1.[OH-].[Na+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[CH:10][C:11]([NH:14][C:15]2[CH:24]=[CH:23][C:22]([CH:25]3[CH2:26][CH2:27]3)=[CH:21][C:16]=2[C:17]([OH:19])=[O:18])=[CH:12][N:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57479010HCID 57479010, compound

Product 1

HCID 569684702-(2-(2-Chlorophenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acidYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The solid residue obtained in step A was dissolved in methanol (3 ml) and aqueous solution 2N NaOH (1 ml) was added. The mixture was heated at 60° C. for 2 hours, the solvent was evaporated and the solid obtained was suspended in water. The pH was taken to 6.5 and extracted with CHCl3. The crude mixture was purified over a SiO2 eluting with DCM/MeOH 2% affording 0.170 g (yield 81%) of the expected product.

Workup

  1. customthe solvent was evaporated
  2. customthe solid obtained
  3. extractionextracted with CHCl3
  4. customThe crude mixture was purified over a SiO2 eluting with DCM/MeOH 2%

Sources & evidence

ORD record
ord-5f9f7668ae5242c081121df1294b9a7b
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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