Ammonia → 4-Chloro-5-(4-ethylphenyl)-6-(2-fluorophenyl)furo[2,3-d]pyrimidine

HRID 2189067Notes

Reaction equation

HRID 2189067 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16](=O)[NH:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])=[CH:5][CH:4]=1)[CH3:2].P(Cl)(Cl)([Cl:28])=O.N>O>[Cl:28][C:16]1[C:17]2[C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=3)=[C:10]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[O:11][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 58016929HCID 58016929, compound

Product 1

HCID 580167964-Chloro-5-(4-ethylphenyl)-6-(2-fluorophenyl)furo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Stir a suspension of 20.0 g (0.06 mol) 5-(4-ethylphenyl)-6-(2-fluorophenyl)furo[2,3-d]pyrimidin-4(3H)-one in 100 ml (165 g, 1.07 mol) phosphoryl chloride for 1 h at 120° C. After cooling to room temperature, add the reaction solution dropwise to a mixture of 330 ml water and 610 ml 25% aqueous ammonia solution, stirring vigorously; a temperature rise to 55-65° C. is observed. Leave the reaction mixture to cool to room temperature. After extracting twice with 500 ml dichloromethane each time, wash the organic phase with satd. aqueous sodium chloride solution, dry over sodium sulphate and filter. Concentrate the filtrate by vacuum evaporation. Mix the residue with 150 ml petroleum ether, filter, wash with ice-cooled petroleum ether and dry under vacuum. 18.7 g (90% purity, 80% of theor.) of the title compound is obtained.

Workup

  1. additionadd the reaction solution
  2. stirringstirring vigorously
  3. customto 55-65° C.
  4. customLeave the reaction mixture
  5. temperatureto cool to room temperature
  6. extractionAfter extracting twice with 500 ml dichloromethane each time
  7. washwash the organic phase with satd
  8. dry with materialaqueous sodium chloride solution, dry over sodium sulphate
  9. filtrationfilter
  10. concentrationConcentrate the filtrate
  11. customby vacuum evaporation
  12. additionMix the residue with 150 ml petroleum ether
  13. filtrationfilter
  14. washwash with ice-
  15. temperaturecooled petroleum ether
  16. customdry under vacuum

Sources & evidence

ORD record
ord-5e74216d403242c7ac5cc37c57866474
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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