5-nitro-2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidine → 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidin-5-amine

HRID 537491Notes

Reaction equation

HRID 537491 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]([N:10]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[N:11]2)=[N:8][CH:9]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[F:18][C:15]([F:16])([F:17])[C:13]1[CH:12]=[N:11][N:10]([C:7]2[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][N:6]=2)[CH:14]=1

Participants

4

Reactant 1

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

Product 1

HCID 641756422-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidin-5-amineYield 170.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A Parr Shaker bottle was charged with Pd/C (10% wet; degussa type; 300 mg) and the 5-nitro-2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidine (1.18 g, 4.55 mmol) in ethyl acetate (91 mL). Shaked at 40 psi of H2 (g) for 8 hours. Crude mixture filtered through celite and concentrated under reduced pressure to afford 2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidin-5-amine (1.78 g, 98%) as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ 5.85 (s, 2H) 8.15 (s, 1H) 8.18 (s, 2H) 8.95 (s, 1H); MS (M+1): 230.2.

Workup

  1. filtrationCrude mixture filtered through celite and
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-714c56789fd246dbbd7ffa83046603ba
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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