Lithium hydroxide, monohydrate → 4-(5-Chloro-2-cyclopropylaminopyrimidin-4-yl)benzoic acid

HRID 968691Notes

Reaction equation

HRID 968691 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15]([Cl:16])=[CH:14][N:13]=[C:12]([NH:17][CH:18]3[CH2:20][CH2:19]3)[N:11]=2)=[CH:6][CH:5]=1.O.[OH-].[Li+]>C1COCC1.O.Cl>[Cl:16][C:15]1[C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:21])=[O:2])=[CH:5][CH:6]=2)=[N:11][C:12]([NH:17][CH:18]2[CH2:20][CH2:19]2)=[N:13][CH:14]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69422210Methyl 4-(5-chloro-2-(cyclopropylamino)pyrimidin-4-yl)benzoate

Product 1

HCID 694221834-(5-Chloro-2-cyclopropylaminopyrimidin-4-yl)benzoic acidYield 90%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

4-(5-Chloro-2-cyclopropylaminopyrimidin-4-yl)-benzoic acid methyl ester (90 mg, 0.30 mmol) was dissolved in THF and 50 mg (1.2 mmol) of lithium hydroxide monohydrate dissolved in water was added. The reaction mixture was heated to 50° C. for 5 hours, cooled to room temperature, diluted with 1N HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to afford 4-(5-chloro-2-cyclopropylaminopyrimidin-4-yl)-benzoic acid as a yellow solid, 78 mg, 0.27 mmol, 90% yield.

Workup

  1. additionwas added
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4a2d16a19aa74ccda9d7fbb4ac6d9b99
Source dataset
uspto-grants-2007_12
Patent number
US07304071B2

Reaction notes

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