Lithium Hydroxide → 2-Chloro-4-(3-fluoro-4-(thiazol-4-yl)phenylamino)pyrimidine-5-carboxylic acid

HRID 1846697Notes

Reaction equation

HRID 1846697 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:16]=[CH:17][S:18][CH:19]=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]([C:15]3[N:16]=[CH:17][S:18][CH:19]=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 57471881Ethyl 2-chloro-4-(3-fluoro-4-(thiazol-4-yl)phenylamino)pyrimidine-5-carboxylate

Product 1

HCID 574718822-Chloro-4-(3-fluoro-4-(thiazol-4-yl)phenylamino)pyrimidine-5-carboxylic acidYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of ethyl 2-chloro-4-(3-fluoro-4-(thiazol-4-yl)phenylamino)pyrimidine-5-carboxylate (186 mg, 0.491 mmol) in THF (4 mL), aq. 1N LiOH (1.00 mL, 1.00 mmol) was added. The suspension became clear with stirring. The mixture was then 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-(3-fluoro-4-(thiazol-4-yl)phenylamino)pyrimidine-5-carboxylic acid (158 mg). MS 351.2 and 353.3 (M+H, Cl pattern)

Workup

  1. additionwas added
  2. stirringThe mixture was then stirred at room temperature overnight
  3. customUpon acidification of the mixture with 1N HCl, white solids precipitated out
  4. customwhich were collected
  5. customdried on vacuum

Sources & evidence

ORD record
ord-eb89c90e11a94b27824bbb227b80f3fd
Source dataset
uspto-grants-2015_02
Patent number
US08952027B2

Reaction notes

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