Hydrochloric Acid → 3-(3-Chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-5-carboxylic acid

HRID 1443841Notes

Reaction equation

HRID 1443841 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]2[N:12]=[CH:13][C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)=[C:8]2[N:7]=1)=[O:5])C.CO.[OH-].[Na+].Cl>O1CCCC1>[Cl:21][C:17]1[CH:16]=[C:15]([C:14]2[CH:13]=[N:12][N:9]3[CH:10]=[CH:11][C:6]([C:4]([OH:5])=[O:3])=[N:7][C:8]=23)[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 586288723-(3-Chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 586287193-(3-Chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-5-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-(3-chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-5-carboxylic acid ethyl ester (18.00 g), 120 ml of methanol, and 120 ml of tetrahydrofuran, 60 ml of a 2N aqueous sodium hydroxide solution was added, and stirred at room temperature over 2 hours. To the reactant, 60 ml of 2N hydrochloride was added dropwise, and the precipitated crystal was filtered to yield 3-(3-chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-5-carboxylic acid (14.02 g, 86%) as a yellow crystal.

Workup

  1. additionwas added
  2. filtrationthe precipitated crystal was filtered

Sources & evidence

ORD record
ord-575b3460ba754ad1a9e3a698ba8313e7
Source dataset
uspto-grants-2010_02
Patent number
US07662826B2

Reaction notes

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