Cesium carbonate → HCID 57400816, compound

HRID 1773142Notes

Reaction equation

HRID 1773142 reaction equation
Br[CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[CH:6][CH:7]=1.[NH:17]1[CH:24]=[CH:23][C:21]([NH2:22])=[N:20][C:18]1=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[NH2:22][C:21]1[CH:23]=[CH:24][N:17]([CH2:2][C:3]2[O:4][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N+:14]([O-:16])=[O:15])=[CH:6][CH:7]=2)[C:18](=[O:19])[N:20]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 12631380HCID 12631380, compoundHCID 178418229Cytosine

Product 1

HCID 57400816HCID 57400816, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(bromomethyl)-5-(2-nitrophenyl)furan 11a (230 mg, 0.815 mmol) and cytosine 14a (181 mg, 1.63 mmol) in anhydrous DMF (4 mL) was added cesium carbonate (398 mg, 1.22 mmol) at 25° C. The resulting solution was stirred for 12 h at the same temperature. After removal of the DMF under reduced pressure, the residue was diluted with CHCl3 and washed three times with water. The organic layer was dried over anhydrous MgSO4 and concentrated in a vacuum. The residue was purified by column chromatography eluting with ethyl acetate/methanol (20:1) to afford 170 mg (67%) of the cytosine 15a as a white solid. 1H NMR (DMSO) δ: 7.87 (1H, d, J=8.0 Hz), 7.82 (1H, d, J=7.5 Hz), 7.73 (1H, t, J=7.5 Hz), 7.58 (1H, d, J=7.0 Hz), 7.56 (1H, t, J=8.5 Hz), 7.16 (1H, s), 7.09 (1H, s), 6.86 (1H, d, J=3.5 Hz), 6.48 (1H, d, J=3.0 Hz), 5.72 (1H, d, J=7.5 Hz), 4.89 (2H, s); 13C NMR δ: 166.33, 155.63, 152.62, 147.82, 147.11, 145.59, 132.72, 129.41, 128.80, 124.16, 122.73, 110.07, 110.92, 94.21, 44.57.

Workup

  1. customAfter removal of the DMF under reduced pressure
  2. additionthe residue was diluted with CHCl3
  3. washwashed three times with water
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated in a vacuum
  6. customThe residue was purified by column chromatography
  7. washeluting with ethyl acetate/methanol (20:1)

Sources & evidence

ORD record
ord-47c77b9bbd8d4c3b9c0eba746721a406
Source dataset
uspto-grants-2016_02
Patent number
US09255088B2

Reaction notes

Loading…