Phosphorus oxychloride → 4-chloro-5H-pyrrolo[3,2-d]pyrimidine

HRID 532469Notes

Reaction equation

HRID 532469 reaction equation
[N:1]1[C:6]2[CH:7]=[CH:8][NH:9][C:5]=2[C:4](=O)[NH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:13]>>[Cl:13][C:4]1[C:5]2[NH:9][CH:8]=[CH:7][C:6]=2[N:1]=[CH:2][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1354888819-Deazahypoxanthine

Product 1

HCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidine

Procedure

To 3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one (1.8 g), POCl3 (5 mL) was added, and refluxed while stirring. After completion of the reaction, the reaction mixture was distilled under reduced pressure to remove POCl3. Then, the reaction mixture was mixed with ethyl acetate, washed with saturated sodium bicarbonate and washed with a saline solution. The washed mixture was dried over anhydrous sodium sulfate, and filtered and distilled under reduced pressure to obtain the title compound.

Workup

  1. temperaturerefluxed
  2. customAfter completion of the reaction
  3. distillationthe reaction mixture was distilled under reduced pressure
  4. customto remove POCl3
  5. additionThen, the reaction mixture was mixed with ethyl acetate
  6. washwashed with saturated sodium bicarbonate
  7. washwashed with a saline solution
  8. dry with materialThe washed mixture was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-97dcda288a1e498bbeec3d35753774fa
Source dataset
uspto-grants-2014_10
Patent number
US08853213B2

Reaction notes

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