Cesium carbonate → HCID 21069279, compound

HRID 531452Notes

Reaction equation

HRID 531452 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[N:8]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOCC>[N:3]1[CH:4]=[CH:5][N:6]=[CH:7][C:2]=1[N:11]1[CH2:10][CH2:9][N:8]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 73277ChloropyrazineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 21069279HCID 21069279, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloropyrazine (2.13 g, 18.7 mmol), tert-butyl piperazine-1-carboxylate (3.16 g, 17 mmol) and caesium carbonate (7.7 g, 23.7 mmol) in DMF (35 ml) was heated at 100° C. for 16 hours. Cooled to RT and diluted with ether. Ether layer was washed with water and brine, dried over sodium sulphate and distilled off the solvent to afford 2 g (40.7% yield) of the titled product after purification with (60/120 silica gel) column chromatography using 40% ethyl acetate in hexane as eluent.

Workup

  1. temperatureCooled to RT
  2. washEther layer was washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. distillationdistilled off the solvent

Sources & evidence

ORD record
ord-8e8853b59f5140739e76e57c8578521d
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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