Piperazine → 2-(Piperazin-1-yl)-4-(trifluoromethyl)pyrimidine

HRID 1436792Notes

Reaction equation

HRID 1436792 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH: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>[N:12]1([C:2]2[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 8471TriethylamineHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidine

Product 1

HCID 27783342-(Piperazin-1-yl)-4-(trifluoromethyl)pyrimidineYield 57.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-4-(trifluoromethyl)pyrimidine (2.0 g, 11 mmol), piperazine (2.8 g, 33 mmol) and triethylamine (3.0 mL, 22 mmol) in DMF (10 mL) was stirred at 100° C. in a sealed tube overnight. After removal of most of the solvent, the residue was purified by column chromatography on silica gel (EtOAc to EtOAc/MeOH/NEt3 9/1/0.5) to give 1.48 g (56%) of desired product. MS calculated for C9H11F3N4:(M+H) 233; found 233.1.

Workup

  1. customAfter removal of most of the solvent
  2. customthe residue was purified by column chromatography on silica gel (EtOAc to EtOAc/MeOH/NEt3 9/1/0.5)

Sources & evidence

ORD record
ord-1d5cef085de84b3db79d9a748878a779
Source dataset
uspto-grants-2009_11
Patent number
US07618970B2

Reaction notes

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