Piperazine → 4-(Piperazin-1-yl)-6-(trifluoromethyl)pyrimidine

HRID 270586Notes

Reaction equation

HRID 270586 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[CH:4][N:3]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)CC)C>CN(C=O)C.O>[N:12]1([C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[CH:4][N:3]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 4837PiperazineHCID 8471TriethylamineHCID 115428814-Chloro-6-(trifluoromethyl)pyrimidine

Product 1

HCID 529877424-(Piperazin-1-yl)-6-(trifluoromethyl)pyrimidineYield 56.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-6-(trifluoromethyl)pyrimidine (1.0 g, 5.48 mmol), piperazine (2.36 g, 27.4 mmol), and triethylamine (2.29 mL, 16.4 mmol) in DMF (20 mL) was stirred at 100° C. for 5 h. The reaction solution was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography (10% MeOH/5% Et3N/EtOAc) to yield the desired product (720 mg, 56.6%). LCMS calculated for C9H12F3N4: (M+1) 233.1; found 233.1.

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash column chromatography (10% MeOH/5% Et3N/EtOAc)

Sources & evidence

ORD record
ord-ec042e2c72d24ee28457c439f75b6726
Source dataset
uspto-grants-2008_11
Patent number
US07449467B2

Reaction notes

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