Hydrogen Bromide → 4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]-pyrimidine hydrobromide

HRID 611549Notes

Reaction equation

HRID 611549 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8](C(C)(C)C)[C:4]=2[N:5]=[CH:6][N:7]=1.[BrH:28]>C(O)(=O)C>[BrH:28].[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][CH:16]=3)=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 99506787-tert-Butyl-5-(4-phenoxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Product 1

HCID 227362304-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]-pyrimidine hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-amino-5-(4-phenoxyphenyl)-7-(tert-butyl)pyrrolo[2,3-d]-pyrimidine (5.8 g), glacial acetic acid (55 ml) and hydrobromic acid (55 ml of a 48% solution) was boiled under reflux for 18 hours under nitrogen. The mixture was allowed to cool and a solid was collected by filtration. This solid was washed with methanol and then with ether to give 4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]-pyrimidine hydrobromide, m.p. 288-292° C. The hydrobromide salt was converted into the free base by warming with dilute sodium hydroxide solution (100 ml of 5% w/v solution) and ethanol (60 ml) with stirring and removing the ethanol by distillation. The mixture was cooled and the solid was collected by filtration and washed well with water to give 5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine.

Workup

  1. temperatureunder reflux for 18 hours under nitrogen
  2. temperatureto cool
  3. filtrationa solid was collected by filtration
  4. washThis solid was washed with methanol

Sources & evidence

ORD record
ord-21845e4985584facadb4190d703acc7b
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

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