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

HRID 588376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588376
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 1176527814-(Pyrazolo[1,5-a]pyrimidin-3-yl)benzoic acidAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-af52a6633a534a458393ec99ae0e1b03
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227956B2

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