Water → HCID 19597402, compound

HRID 611537Notes

Reaction equation

HRID 611537 reaction equation
S([O-])(O[O-])(=O)=[O:2].[K+].[K+].[NH2:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([S:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)=[CH:17][N:16]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:12]=2[N:13]=[CH:14][N:15]=1.[OH2:36]>CO.C(O)(=O)C>[C:32]([N:16]1[C:12]2[N:13]=[CH:14][N:15]=[C:10]([NH2:9])[C:11]=2[C:18]([C:19]2[CH:20]=[CH:21][C:22]([S:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:2])=[O:36])=[CH:23][CH:24]=2)=[CH:17]1)([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 3

HCID 962Water2×HCID 10313463Potassium peroxymonosulphateHCID 19597401HCID 19597401, compound

Product 1

HCID 19597402HCID 19597402, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of potassium peroxymonosulphate (4.93g) in water (10 ml) was added dropwise with stirring to a solution of 4-amino-5-[4-(phenylthio)phenyl]-7-(tert-butyl)pyrrolo[2,3-d]pyrimidine (1.0 g) in methanol (5 ml) and glacial acetic acid (5 ml) keeping the temperature below 5° C. The mixture was then stirred at ambient temperature for 3 hours and then diluted with water (50 ml). The mixture was extracted with ethyl acetate to give a solid which was purified by flash column chromatography on silica using ethyl acetate/triethylamine (9:1) as the mobile phase. Appropriate fractions were combined and concentrated to give a solid which was triturated with petroleum ether, boiling point 60-80° C. to give 7-tert-butyl-5-(4-phenylsulphonylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine, m.p. 222-224° C.

Workup

  1. customthe temperature below 5° C
  2. extractionThe mixture was extracted with ethyl acetate
  3. customto give a solid which
  4. customwas purified by flash column chromatography on silica
  5. concentrationconcentrated
  6. customto give a solid which
  7. customwas triturated with petroleum ether, boiling point 60-80° C.

Sources & evidence

ORD record
ord-7c6645afdfef46098b1eb5db763bf6b9
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

Loading…