Cesium carbonate → HCID 86732282, compound

HRID 930469Notes

Reaction equation

HRID 930469 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[O:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH2:17][OH:18].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[O:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH2:17][O:18][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 406081Methyl 5-chloropyrazine-2-carboxylateHCID 14786610(1,3-Oxazol-2-yl)methanol

Product 1

HCID 86732282HCID 86732282, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a flask was added methyl 5-chloropyrazine-2-carboxylate (1.5179 g, 8.80 mmol), oxazol-2-ylmethanol (0.697 ml, 8.80 mmol), and cesium carbonate (0.845 ml, 10.56 mmol) in DMF (25.1 mL) to stir at 40° C. for 24 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic extract was washed with water, brine, and dried over MgSO4, filtered and concentrated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (100 g), eluting with a gradient of 10-100% EtOAc/hexane, to provide methyl 5-(oxazol-2-ylmethoxy)pyrazine-2-carboxylate (0.547 g, 2.327 mmol, 26.5% yield). MS m/z=236.0 [M+H]+. Calculated for C10H9N3O4: 235.059

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customchromatographed through a Biotage SNAP HP-silica gel column (100 g)
  8. washeluting with a gradient of 10-100% EtOAc/hexane

Sources & evidence

ORD record
ord-0e48cceb0e5a4cf9a14373a92f9611d0
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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