Ammonia → N-[4-(4-amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl]benzenesulphonamide

HRID 611534Notes

Reaction equation

HRID 611534 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)(=[O:20])=[O:19])=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:27]([CH3:29])[CH3:28])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:30]>O1CCOCC1>[NH2:30][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)(=[O:20])=[O:19])=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:27]([CH3:29])[CH3:28])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 19597404N-[4-(4-chloro-7-isopropylpyrrolo[2,3-d]pyrimidin-5-yl)phenyl]benzenesulphonamide

Product 1

HCID 19597485N-[4-(4-amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl]benzenesulphonamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-[4-(4-chloro-7-isopropylpyrrolo[2,3-d]pyrimidin-5-yl)phenyl]-benzenesulphonamide (0.34 g), concentrated ammonia (30 ml, SG 0.880) and 1,4-dioxane (30 ml) was heated with stirring at 120° C. in a pressure vessel for 16 hours. The mixture was allowed to cool to ambient temperature and the solvent was removed under reduced pressure to give a residue which was partitioned between water (40 ml) and ethyl acetate (40 ml). The organic layer was separated and the aqueous layer was further extracted with ethyl acetate (2×40 ml). The combined ethyl acetate extracts were washed, dried, filtered and evaporated to give a solid which was purified by flash column chromatography on silica using ethyl acetate/cyclohexane (8:2) as the mobile phase. Appropriate fractions were collected, combined and concentrated to give N-[4-(4-amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl]benzenesulphonamide, m.p. 238-240° C.

Workup

  1. temperaturewas heated
  2. temperatureto cool to ambient temperature
  3. customthe solvent was removed under reduced pressure
  4. customto give a residue which
  5. customwas partitioned between water (40 ml) and ethyl acetate (40 ml)
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was further extracted with ethyl acetate (2×40 ml)
  8. washThe combined ethyl acetate extracts were washed
  9. customdried
  10. filtrationfiltered
  11. customevaporated
  12. customto give a solid which
  13. customwas purified by flash column chromatography on silica
  14. customAppropriate fractions were collected
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-81e8ef1e7f2b4b50b35b1752038391e2
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

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