Ethyl Acetate → 4-Chloro-6-(biphen-4-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 369841Notes

Reaction equation

HRID 369841 reaction equation
[C:1]1([C:13]2[NH:22][C:16]3[N:17]=[CH:18][N:19]=[C:20](O)[C:15]=3[CH:14]=2)[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.C(OCC)(=O)C.P(Cl)(Cl)([Cl:31])=O>>[Cl:31][C:20]1[C:15]2[CH:14]=[C:13]([C:1]3[CH:6]=[CH:5][C:4]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[CH:3][CH:2]=3)[NH:22][C:16]=2[N:17]=[CH:18][N:19]=1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 178518052HCID 178518052, compound

Product 1

HCID 857171974-Chloro-6-(biphen-4-yl)-7H-pyrrolo[2,3-d]pyrimidine

Procedure

Under a protective gas, 430.5 mg (1.5 mmol) of 6-(biphen-4-yl)-7H-pyrrolo[2,3-d]-pyrimidin-4-ol in 6 ml of phosphorus oxychloride are heated at boiling for 4 hours. The reaction mixture is poured into ice-water and ethyl acetate. The aqueous phase is separated off and extracted with ethyl acetate. Concentrating the organic phases by evaporation and stirring the residue in hot THF/isopropanol yield the title compound; m.p. 295-300° C. (decomposition); FAB-MS: (M+H)+ =306.

Workup

  1. customThe aqueous phase is separated off
  2. extractionextracted with ethyl acetate
  3. concentrationConcentrating the organic phases
  4. customby evaporation

Sources & evidence

ORD record
ord-6daad50212304a35ae0d6d49042df3eb
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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