Cesium carbonate → 6-Chloro-N-cyclopropylpyrazin-2-amine

HRID 634135Notes

Reaction equation

HRID 634135 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[CH:9]1([NH2:12])[CH2:11][CH2:10]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(Cl)Cl>[Cl:8][C:4]1[N:3]=[C:2]([NH:12][CH:9]2[CH2:11][CH2:10]2)[CH:7]=[N:6][CH:5]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 69828CyclopropylamineHCID 785042,6-Dichloropyrazine

Product 1

HCID 467386496-Chloro-N-cyclopropylpyrazin-2-amineYield 76.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A glass microwave reaction vessel was charged with 2,6-dichloropyrazine (1.0 g, 6.71 mmol) and cyclopropanamine (0.383 g, 6.71 mmol) in DMF (4 mL) followed by cesium carbonate (2.187 g, 6.71 mmol). The reaction was stirred and heated in an oil bath at 100° C. for 15 h, then cooled to RT. The mixture was diluted with DCM and washed with H2O. The organic layer was dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 5-10% EtOAc in Hex) to give 6-chloro-N-cyclopropylpyrazin-2-amine (0.87 g, 5.13 mmol, 76%) as a yellow solid. MS (ESI, pos. ion) m/z: 170 (M+1).

Workup

  1. customA glass microwave reaction vessel
  2. temperaturecooled to RT
  3. washwashed with H2O
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with silica gel chromatography (eluting with 5-10% EtOAc in Hex)

Sources & evidence

ORD record
ord-ba629258891a4dd4b91abcd455b8e558
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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