Phosphorus oxychloride → 4-Chloro-5,6-diphenylfuro[2,3-d]pyrimidine

HRID 2189021Notes

Reaction equation

HRID 2189021 reaction equation
[C:1]1([C:7]2[C:15]3[C:14](=O)[NH:13][CH:12]=[N:11][C:10]=3[O:9][C:8]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:14]1[C:15]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:9][C:10]=2[N:11]=[CH:12][N:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 112431895,6-Diphenylfuro[2,3-d]pyrimidin-4-ol

Product 1

HCID 114496374-Chloro-5,6-diphenylfuro[2,3-d]pyrimidine

Procedure

Add 570 ml of phosphorus oxychloride to 57 g (200 mmol) of 5,6-diphenylfuro[2,3-d]pyrimidin-4(3H)-one. Stir the mixture under reflux for 3 h, then cool it and concentrate it under reduced pressure. Stir the residue with ice-water for 30 min and then admix it with dichloromethane. Wash the resulting organic phase three times with water, dry it over sodium sulphate and concentrate it under reduced pressure. 58 g (93.2% of theory) of the target product are obtained.

Workup

  1. temperatureunder reflux for 3 h
  2. temperaturecool it
  3. concentrationconcentrate it under reduced pressure
  4. stirringStir the residue with ice-water for 30 min
  5. washWash the resulting organic phase three times with water
  6. dry with materialdry it over sodium sulphate
  7. concentrationconcentrate it under reduced pressure
  8. custom58 g (93.2% of theory) of the target product are obtained

Sources & evidence

ORD record
ord-9c58f2f42c144794bfa46ed250f19865
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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