Sodium Hydroxide → 5-(6-Trifluoromethyl-pyridin-2-ylamino)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 474349

Reaktionsgleichung

Reaktionsgleichung von HRID 474349
[F:1][C:2]([F:25])([F:24])[C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][N:13]3[N:16]=[CH:17][C:18]([C:19]([O:21]CC)=[O:20])=[C:12]3[N:11]=2)[CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C>[F:24][C:2]([F:1])([F:25])[C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][N:13]3[N:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[C:12]3[N:11]=2)[CH:6]=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 58063370Ethyl 5-(6-(trifluoromethyl)pyridin-2-ylamino)pyrazolo[1,5-a]pyrimidine-3-carboxylate

Produkt 1

HCID 580631475-(6-Trifluoromethyl-pyridin-2-ylamino)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acidAusbeute 112,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl 5-(6-(trifluoromethyl)pyridin-2-ylamino)pyrazolo[1,5-a]pyrimidine-3-carboxylate (344 mg, 0.98 mmol, 1.0 equiv), 2M aqueous sodium hydroxide solution (1.50 mL, 3.0 equiv) and ethanol (15 mL) was heated to reflux for 5 hours. After cooling, the precipitate was collected by filtration, washed with ethanol, and air dried. The resultant solid was suspended in 1.25 M HCl in methanol (16 mL) and then concentrated under vacuum. The residue was triturated (diethyl ether) to afford 355 mg (quant. yield) of 5-(6-trifluoromethyl-pyridin-2-ylamino)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid which was used without further purification. LCMS (ESI) m+H=324.2; 1H NMR (300 MHz, DMSO-d6) δ: 11.03 (s, 1H), 9.01 (d, 1H), 8.95 (d, 1H), 8.35 (s, 1H), 8.10-8.02 (m, 1H), 7.54 (d, 1H), 7.16 (d, 1H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with ethanol, and air
  6. customdried
  7. concentrationconcentrated under vacuum
  8. customThe residue was triturated (diethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-0d445c8ca0c942b7947d83ea47e731a2
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637526B2

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