Lithium Hydroxide → 2-chloro-4-(3-fluoro-4-(1H-imidazol-1-yl)phenylamino)pyrimidine-5-carboxylic acid

HRID 1880281Notes

Reaction equation

HRID 1880281 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH:19]=[CH:18][N:17]=[CH:16]3)=[C:11]([F:20])[CH:10]=2)[C:5]([C:21]([O:23]CC)=[O:22])=[CH:4][N:3]=1.[Li+].[OH-]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH:19]=[CH:18][N:17]=[CH:16]3)=[C:11]([F:20])[CH:10]=2)[C:5]([C:21]([OH:23])=[O:22])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57471885ethyl 2-chloro-4-(3-fluoro-4-(1H-imidazol-1-yl)phenylamino)pyrimidine-5-carboxylate

Product 1

HCID 574718862-chloro-4-(3-fluoro-4-(1H-imidazol-1-yl)phenylamino)pyrimidine-5-carboxylic acidYield 19.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-chloro-4-(3-fluoro-4-(1H-imidazol-1-yl)phenylamino)pyrimidine-5-carboxylate (383 mg, 1.06 mmol) in THF (5 mL), aq. 1N LiOH (2.00 mL, 2.00 mmol) was added. The mixture was stirred at room temperature overnight. THF was removed in vacuo. Upon acidification with 1N HCl, the mixture was purified by HPLC to give 2-chloro-4-(3-fluoro-4-(1H-imidazol-1-yl)phenylamino)pyrimidine-5-carboxylic acid (68 mg). MS 334.1 and 336.1 (M+H, Cl pattern)

Workup

  1. customTHF was removed in vacuo
  2. customUpon acidification with 1N HCl, the mixture was purified by HPLC

Sources & evidence

ORD record
ord-aa1b354a30784b69ad1ebe9cdb2ae946
Source dataset
uspto-grants-2012_11
Patent number
US08318755B2

Reaction notes

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