Sodium Hydroxide → 4-(Pyrazolo[1,5-a]pyrimidin-3-yl)benzoic acid

HRID 588376Notes

Reaction equation

HRID 588376 reaction equation
[N:1]1[N:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]2=[C:3]([C:10]2[CH:20]=[CH:19][C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][CH:11]=2)[CH:2]=1.[OH-].[Na+]>CO>[N:1]1[N:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]2=[C:3]([C:10]2[CH:20]=[CH:19][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117652969Ethyl 4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzoate

Product 1

HCID 1176527814-(Pyrazolo[1,5-a]pyrimidin-3-yl)benzoic acidYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of the compound form Step 1 ethyl 4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzoate (64 g, 0.24 mol) in MeOH (1 L) was added an aqueous solution of sodium hydroxide (600 mL, 1.2 mol, 2 M). The mixture was heated at 50° C. for 3 h. The mixture was then concentrated to remove the volatiles. The resulting suspension was diluted with water, and aqueous HCl (1 N) was added dropwise until pH 4. The acidified suspension was filtered, and the solids were collected and dried to give the title compound (57 g, 99%) as a yellow solid.

Workup

  1. concentrationThe mixture was then concentrated
  2. customto remove the volatiles
  3. additionThe resulting suspension was diluted with water, and aqueous HCl (1 N)
  4. additionwas added dropwise until pH 4
  5. filtrationThe acidified suspension was filtered
  6. customthe solids were collected
  7. customdried

Sources & evidence

ORD record
ord-af52a6633a534a458393ec99ae0e1b03
Source dataset
uspto-grants-2016_01
Patent number
US09227956B2

Reaction notes

Loading…