Phosphorus oxychloride → 4-Chloro-6-(naphth-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 369844Notes

Reaction equation

HRID 369844 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[NH:20][C:14]2[N:15]=[CH:16][N:17]=[C:18](O)[C:13]=2[CH:12]=1.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:18]1[C:13]2[CH:12]=[C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)[NH:20][C:14]=2[N:15]=[CH:16][N:17]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178518051HCID 178518051, compound

Product 1

HCID 232827174-Chloro-6-(naphth-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

Procedure

Under a protective gas, 198.5 mg (0.76 mmol) of 6-(naphth-2-yl)-7H-pyrrolo[2,3-d]-pyrimidin-4-ol in 3 ml of phosphorus oxychloride are heated at boiling for 5 hours. The reaction mixture is poured into ice-water and stirred for 1 hour to complete the reaction. The crystals are filtered off and washed with water. Dissolving the crude product in THF/methanol, filtering through active carbon, concentrating the filtrate by evaporation, stirring the residue in isopropanol and washing with hexane yield the title compound; m.p. 268-269° C. (decomposition); FAB-MS: (M+H)+ =280.

Workup

  1. customthe reaction
  2. filtrationThe crystals are filtered off
  3. washwashed with water
  4. dissolutionDissolving the crude product in THF/methanol
  5. filtrationfiltering through active carbon
  6. concentrationconcentrating the filtrate
  7. customby evaporation
  8. stirringstirring the residue in isopropanol
  9. washwashing with hexane

Sources & evidence

ORD record
ord-d7c81039d7ed4f4680212978615c75cd
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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