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

HRID 474349

Reaction equation

HRID 474349 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 580631475-(6-Trifluoromethyl-pyridin-2-ylamino)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acidYield 112.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-0d445c8ca0c942b7947d83ea47e731a2
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Linked notes

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