Ammonium formate → 5-[4-(2-Amino-phenoxy)-phenyl]-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

HRID 611527Notes

Reaction equation

HRID 611527 reaction equation
[CH:1]([N:4]1[C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH2:13])[C:7]=2[C:6]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N+:27]([O-])=O)=[CH:16][CH:15]=2)=[CH:5]1)([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].C(O)C>[NH2:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[O:20][C:17]1[CH:16]=[CH:15][C:14]([C:6]2[C:7]3[C:12]([NH2:13])=[N:11][CH:10]=[N:9][C:8]=3[N:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 195974577-isopropyl-5-[4-(2-nitrophenoxy)phenyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Product 1

HCID 195974765-[4-(2-Amino-phenoxy)-phenyl]-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-isopropyl-5-[4-(2-nitrophenoxy)phenyl]-7H-pyrrolo[2,3-d]-pyrimidin-4-ylamine (0.15 g), ammonium formate (3 equivalents), 10% palladium on charcoal (15 mg) and ethanol (5 ml) was boiled under reflux under nitrogen for 2 hours. Further ammonium formate (100 mg) was added after one hour. The mixture was cooled and filtered through silica. The filter bed was washed with industrial methylated spirit (2×10 ml). The filtrate was evaporated and the residue was extracted with ethyl acetate. The ethyl acetate was removed under reduced pressure to give a residue which was purified by flash column chromatography on silica using ethyl acetate as the mobile phase to give 5-[4-(2-aminophenoxy)phenyl]-7-isopropyl-7H-pyrrolo[2,3-d]-pyrimidin-4-ylamine. The structure was confirmed by 1H nmr.

Workup

  1. temperatureunder reflux under nitrogen for 2 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through silica
  4. washThe filter bed was washed with industrial methylated spirit (2×10 ml)
  5. customThe filtrate was evaporated
  6. extractionthe residue was extracted with ethyl acetate
  7. customThe ethyl acetate was removed under reduced pressure
  8. customto give a residue which
  9. customwas purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-5182d17592f349a5950f2131c4e67a54
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

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