Ammonium Chloride → 5-(4-Aminophenyl)-4-chloro-7-isopropylpyrrolo[2,3-d]pyrimidine

HRID 611532Notes

Reaction equation

HRID 611532 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:20]([CH3:22])[CH3:21])[C:4]=2[N:5]=[CH:6][N:7]=1.[Cl-].[NH4+]>[Fe].O>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:3]3[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=3[N:8]([CH:20]([CH3:22])[CH3:21])[CH:9]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 195974814-Chloro-7-isopropyl-5-(4-nitrophenyl)pyrrolo[2,3-d]pyrimidine

Product 1

HCID 195974875-(4-Aminophenyl)-4-chloro-7-isopropylpyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 4-chloro-7-isopropyl-5-(4-nitrophenyl)pyrrolo[2,3-d]pyrimidine (1.0 g), iron powder (1.76 g), ammonium chloride (86 mg), water (8 ml) and industrial methylated spirit (40 ml) was boiled under reflux for one hour. The mixture was filtered and the solvent evaporated. The residue was taken up in ethyl acetate and washed with water. The ethyl acetate extract was dried, filtered and evaporated to give 5-(4-aminophenyl)-4-chloro-7-isopropylpyrrolo[2,3-d]pyrimidine.

Workup

  1. temperatureunder reflux for one hour
  2. filtrationThe mixture was filtered
  3. customthe solvent evaporated
  4. washwashed with water
  5. extractionThe ethyl acetate extract
  6. customwas dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4836753ec72e49499603987c56851b6e
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

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