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

HRID 369710Notes

Reaction equation

HRID 369710 reaction equation
O[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1785265146-(4-nitrophenyl)-1,7-dihydropyrrolo[2,3-d]pyrimidin-4-one

Product 1

HCID 212626054-Chloro-6-(4-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidine

Procedure

4-Chloro-6-(4-nitro-phenyl)-7H-pyrrolo[2,3-d]pyrimidine is prepared, with the exclusion of moisture, by heating 4-hydroxy-6-(4-nitro-phenyl)-7H-pyrrolo[2,3-d]pyrimidine to boiling point with an excess of POCl3. The suspension is concentrated to a residual volume of 20 ml by evaporation. The residue is introduced in portions into water, neutralized with solid NaHCO3, and 0.2 liter of ethyl acetate is added. Filtration and washing with hot THF yield the title compound, m.p. >280° C.; FAB-MS: (M+H)+ =275.

Workup

  1. custom4-Chloro-6-(4-nitro-phenyl)-7H-pyrrolo[2,3-d]pyrimidine is prepared, with the exclusion of moisture
  2. concentrationThe suspension is concentrated to a residual volume of 20 ml by evaporation
  3. additionThe residue is introduced in portions into water
  4. additionis added
  5. filtrationFiltration
  6. washwashing with hot THF

Sources & evidence

ORD record
ord-66ec825bb3e949e58cd0d18e9f575b76
Source dataset
uspto-grants-2000_10
Patent number
US06140317

Reaction notes

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