Phosphorus oxychloride → 4-Chloro-5-(4-ethylphenyl)-6-iodofuro[2,3-d]pyrimidine

HRID 2189071Notes

Reaction equation

HRID 2189071 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[I:19])=[CH:5][CH:4]=1)[CH3:2].P(Cl)(Cl)([Cl:22])=O>>[Cl:22][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]([I:19])[O:11][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 582801285-(4-Ethylphenyl)-6-iodofuro[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 582802194-Chloro-5-(4-ethylphenyl)-6-iodofuro[2,3-d]pyrimidine

Procedure

Stir a suspension of 1.4 g (85% purity, 3.3 mmol) of 5-(4-ethylphenyl)-6-iodofuro[2,3-d]pyrimidin-4(3H)-one in 20 ml (32.9 g, 214.6 mmol) of phosphoryl chloride under reflux for one hour. After concentrating under reduced pressure, add ice-cold water and dichloromethane to the residue. Dry the organic phase over sodium sulphate and filter. Concentrate the filtrate under reduced pressure and dry. 1.0 g (70% purity, 57% of theory) of the target compound is obtained.

Workup

  1. temperatureunder reflux for one hour
  2. concentrationAfter concentrating under reduced pressure
  3. additionadd ice-cold water and dichloromethane to the residue
  4. dry with materialDry the organic phase over sodium sulphate
  5. filtrationfilter
  6. concentrationConcentrate the filtrate under reduced pressure
  7. customdry
  8. custom1.0 g (70% purity, 57% of theory) of the target compound is obtained

Sources & evidence

ORD record
ord-923de6b6682149d0a03d699a9c1d696b
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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