Lithium Hydroxide → 2-chloro-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxylic acid

HRID 1846747Notes

Reaction equation

HRID 1846747 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][N:13]3[CH3:18])[C:5]([C:19]([O:21]CC)=[O:20])=[CH:4][N:3]=1.[Li+].[OH-]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][N:13]3[CH3:18])[C:5]([C:19]([OH:21])=[O:20])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58014943ethyl 2-chloro-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxylate

Product 1

HCID 574720122-chloro-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-chloro-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxylate (crude from step 1) in THF (4 mL), aq. 1N LiOH (2.25 mL, 2.25 mmol) was added. The mixture was stirred at room temperature overnight. Upon acidification of the mixture with 1N HCl, white solids precipitated out, which were collected, and dried on vacuum to give 2-chloro-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxylic acid (325 mg). MS 303.3, 305.3 (M+H, Cl pattern)

Workup

  1. customUpon acidification of the mixture with 1N HCl, white solids precipitated out
  2. customwhich were collected
  3. customdried on vacuum

Sources & evidence

ORD record
ord-b3b87b0f0b3a49f6b150dd7f0768984b
Source dataset
uspto-grants-2015_02
Patent number
US08952027B2

Reaction notes

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