HCID 19597401, compound → HCID 19597482, compound

HRID 611536Notes

Reaction equation

HRID 611536 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[NH2:7][C:8]1[C:9]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([S:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)=[CH:15][N:14]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:10]=2[N:11]=[CH:12][N:13]=1>O.C(O)(=O)C>[C:30]([N:14]1[C:10]2[N:11]=[CH:12][N:13]=[C:8]([NH2:7])[C:9]=2[C:16]([C:17]2[CH:18]=[CH:19][C:20]([S:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:2])=[CH:21][CH:22]=2)=[CH:15]1)([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 2

HCID 19597401HCID 19597401, compoundHCID 23667635Sodium periodate

Product 1

HCID 19597482HCID 19597482, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of sodium periodate (0.60 g) dissolved in water (16 ml) was added to a solution of 4-amino-5-[4-(phenylthio)phenyl]-7-(tert-butyl)pyrrolo[2,3-d]pyrimidine (1.0 g) in glacial acetic acid (30 ml) with stirring whilst keeping the temperature below 5° C. The mixture was stirred for 66 hours at ambient temperature. The mixture was filtered and the filtrate was added to water (300 ml). This mixture was basified with solid sodium bicarbonate, filtered to remove a small amount of solid which was discarded and the filtrate extracted with ethyl acetate to give a residue which was purified by flash column chromatography on silica using ethyl acetate/triethylamine (9:1) as the mobile phase, to give a solid which was rechromatographed under the same conditions to give 7-tert-butyl-5-(4-phenylsulphinylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine, m.p. 180-182° C.

Workup

  1. customthe temperature below 5° C
  2. stirringThe mixture was stirred for 66 hours at ambient temperature
  3. filtrationThe mixture was filtered
  4. additionthe filtrate was added to water (300 ml)
  5. filtrationfiltered
  6. customto remove a small amount of solid which
  7. extractionthe filtrate extracted with ethyl acetate
  8. customto give a residue which
  9. customwas purified by flash column chromatography on silica
  10. customto give a solid which
  11. customwas rechromatographed under the same conditions

Sources & evidence

ORD record
ord-46ec548c6c5341e6b9a82742375d4e17
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

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