Acetic Acid → 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidin-5-amine

HRID 537459Notes

Reaction equation

HRID 537459 reaction equation
C(O)(=O)C.[N+:5]([C:8]1[CH:9]=[N:10][C:11]([N:14]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[N:15]2)=[N:12][CH:13]=1)([O-])=O>CO.C(OCC)(=O)C.[Fe]>[F:22][C:19]([F:20])([F:21])[C:17]1[CH:16]=[N:15][N:14]([C:11]2[N:12]=[CH:13][C:8]([NH2:5])=[CH:9][N:10]=2)[CH:18]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 681573265-nitro-2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidine

Product 1

HCID 641756422-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidin-5-amineYield 64%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Glacial acetic acid (2.78 g, 46.3 mmol) was slowly added to a solution of 5-nitro-2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidine (1.5 g, 5.8 mmol) and iron powder (1.94 g, 34.7 mmol) in methanol (30 mL). The reaction was stirred at room temperature for 3 hours. The reaction was then diluted with ethyl acetate (50 mL) and filtered through Celite. The filtrate was neutralized with saturated aqueous potassium carbonate. The organic layer was separated and washed with water and brine, dried over sodium sulfate, filtered, and concentrated to give 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidin-5-amine (850 mg, 64%) as a yellow solid. 1H NMR (400 MHz, CDCl3, δ): 8.68 (s, 1H), 8.16 (s, 2H), 7.87 (s, 1H), 3.82 (s, 2H).

Workup

  1. filtrationfiltered through Celite
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d0116114da57423aa2849d11e3e2ea40
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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