Reaction #57279

Reaction equation

5-bromo-2-chloropyrimidine

1,1-dimethylethyl 1-piperazinecarboxylate

→

title compound

Yield 58.0%

1,1-dimethylethyl 4-(5-bromo-2-pyrimidinyl)-1-piperazinecarboxylate

Yield 58.0%

Solvents

1,4-dioxane

water

ethyl acetate

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureat reflux for 2 hours
3. 3
   OtherSeparation of the organic layer
4. 4
   Otherdrying
5. 5
   Filtration(MgSO4), filtration and concentration in vacuo
6. 6
   Otherprovided a residue which
7. 7
   Otherwas purified by silica gel chromatography (40 g silica gel, CHCl3/EtOAc)

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.

Source