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

HRID 244447Notes

Reaction equation

HRID 244447 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]pyrimidineYield 57%

Procedure

A mixture of 3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one, (1.8 g, 13.5 mmol, 1 equiv.) and 50 mL of POCl3 was warmed at reflux for 2 hours, cooled to room temperature, and concentrated in vacuo. The residue was then diluted with 200 mL of water, made basic with solid potassium carbonate and extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo to provide 1.18 g (57%) of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine as a yellow solid which was used without further purification.

Workup

  1. temperaturewas warmed
  2. temperatureat reflux for 2 hours
  3. concentrationconcentrated in vacuo
  4. additionThe residue was then diluted with 200 mL of water
  5. extractionextracted with EtOAc
  6. customThe combined organic layers were dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d164f940dcc44d87bf82e8330833e5a4
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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