Hydrochloric Acid → 4-[6-(1-Methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl]benzoic acid

HRID 1255869Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[N:9][C:10]3[N:11]([N:13]=[CH:14][C:15]=3[C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=3)[CH:12]=2)[CH:4]=[N:3]1.[OH-].[K+].Cl>CO>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[N:9][C:10]3[N:11]([N:13]=[CH:14][C:15]=3[C:16]3[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)[CH:12]=2)[CH:4]=[N:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of methyl 4-[6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl]benzoate (0.5 g, 1.5 mmol) in methanol (7.0 mL) was treated with 1M potassium hydroxide in methanol (6.0 mmol, 6.0 mL) and the resulting solution was heated to 60° C. for 48 hours. The reaction was cooled to room temperature and treated with conc. HCl and evaporated to dryness. The solids were washed with water, filtered and dried in vacuo to give 4-[6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl]benzoic acid as a yellow solid: LC/MS [M+H]=320.0

Workup

temperatureThe reaction was cooled to room temperature
customevaporated to dryness
washThe solids were washed with water
filtrationfiltered
customdried in vacuo

Sources & evidence

ORD record: ord-22724975370247ed9f9201066da1d7d0
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461162B2

Reaction notes

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