Cesium carbonate → HCID 57502457, compound

HRID 1926664Notes

Reaction equation

HRID 1926664 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.C[C:10]1[CH:11]=[N:12][C:13]2[C:22](C=1C)=[CH:21][CH:20]=[C:19]1[C:14]=2N=CC(C)=C1C.C(=O)([O-])[O-:28].[Cs+].[Cs+]>C1(C)C=CC=CC=1.CCOC(C)=O.[Cu](I)I>[Cl:8][C:4]1[N:3]=[C:2]([O:28][CH2:10][CH2:11][NH:12][CH:13]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:14]2)[CH:7]=[N:6][CH:5]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 785042,6-Dichloropyrazine

Product 1

HCID 57502457HCID 57502457, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of n-cyclohexylethanolamine (0.48 g, 3.4 mmol) and 2,6-dichloropyrazine (0.50 g, 3.4 mmol) in toluene (17 mL) was added 3,4,7,8-tetramethyl-1,10-phenanthroline (7.9 mg, 0.034 mmol), copper iodide (0.032 g, 0.17 mmol) and cesium carbonate (2.2 g, 6.7 mmol). The reaction mixture was stirred at 100° C. After 18 h, the reaction mixture was cooled to room temperature, diluted with EtOAc (50 mL), filtered through celite and concentrated. The crude residue was purified by silica gel chromatography (EtOAc/Hexanes gradient) to afford N-{2-[(6-chloropyrazin-2-yl)oxy]ethyl}cyclohexanamine as an orange oil. LRMS (ESI) calculated for C12H18ClN3O [M+H]+, 256.1; found 256.1.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. filtrationfiltered through celite
  3. concentrationconcentrated
  4. customThe crude residue was purified by silica gel chromatography (EtOAc/Hexanes gradient)

Sources & evidence

ORD record
ord-10a99b9f30244f0a926bc3a9be5768f8
Source dataset
uspto-grants-2012_05
Patent number
US08183245B2

Reaction notes

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