Cesium carbonate → HCID 25095385, compound

HRID 2189101Notes

Reaction equation

HRID 2189101 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:25][O:26][C:27](=[O:37])[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[CH3:25][O:26][C:27](=[O:37])[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][C:2]2[C:3]3[C:10]([C:11]4[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=4)=[C:9]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[O:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 25095385HCID 25095385, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Heat 300 mg (0.891 mmol) of 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine, 642 mg (3.65 mmol) of 3-(4-hydroxyphenyl)propanoic acid methyl ester and 435.4 mg (1.34 mmol) of caesium carbonate to 120° C. for 2 h. After cooling, add water and filter off the precipitated crude product. Dissolve the solid in ethyl acetate and wash the solution twice with buffer solution (pH 7), dry over magnesium sulphate and concentrate again. After treating the residue with methanol, a solid precipitates out. Filter it off, wash with a little methanol and dry under reduced pressure. 160 mg (36.3% of theory) of the target compound are obtained as a colourless solid.

Workup

  1. temperatureAfter cooling
  2. filtrationfilter off the
  3. customprecipitated crude product
  4. dissolutionDissolve the solid in ethyl acetate
  5. washwash the solution twice with buffer solution (pH 7)
  6. dry with materialdry over magnesium sulphate
  7. concentrationconcentrate again
  8. additionAfter treating the residue with methanol
  9. customa solid precipitates out
  10. filtrationFilter it off,
  11. washwash with a little methanol
  12. customdry under reduced pressure
  13. custom160 mg (36.3% of theory) of the target compound are obtained as a colourless solid

Sources & evidence

ORD record
ord-1fb243477c02409dbe589664162a70c0
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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