tert-Butyl piperazine-1-carboxylate → tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate

HRID 29001Notes

Reaction equation

HRID 29001 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[N:9]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>O1CCOCC1.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:11][CH2:10][N:9]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13]2)=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 21914476tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylateYield 58%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-bromo-2-chloropyrimidine (5.17 mmol) and 1,1-dimethylethyl 1-piperazinecarboxylate (11.4 mmol) in 1,4-dioxane (10 ml) was heated at reflux for 2 hours. After cooling to room temperature, the reaction mixture was diluted with water (100 ml) and ethyl acetate (100 ml). Separation of the organic layer, drying (MgSO4), filtration and concentration in vacuo provided a residue which was purified by silica gel chromatography (40 g silica gel, CHCl3/EtOAc) to give the title compound as a white solid (58%). ESMS [M+H-Boc]+: 245.0/243.0.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customSeparation of the organic layer
  4. customdrying
  5. filtration(MgSO4), filtration and concentration in vacuo
  6. customprovided a residue which
  7. customwas purified by silica gel chromatography (40 g silica gel, CHCl3/EtOAc)

Sources & evidence

ORD record
ord-7e3f5a82c4654e8ca0222ca8d720a2d1
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

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