Chlorosuccinimide → HCID 19597513, compound

HRID 611535Notes

Reaction equation

HRID 611535 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:28]N1C(=O)CCC1=O>ClCCl>[C:24]([N:8]1[C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=2[C:10]([C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:16]=2)=[C:9]1[Cl:28])([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 99506787-tert-Butyl-5-(4-phenoxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Product 1

HCID 19597513HCID 19597513, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-amino-5-(4-phenoxyphenyl)-7-(tert-butyl)pyrrolo[2,3-d]-pyrimidine (0.20 g), N-chlorosuccinimide (80 mg) and dichloromethane (5 ml) was stirred at ambient temperature for 18 hours. The mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried and evaporated to give an oil which was purified by flash column chromatography on silica using ethyl acetate/triethylamine (95:5) as the mobile phase. Appropriate fractions were collected, combined and evaporated to give 7-(tert-butyl)-6-chloro-5-(4-phenoxyphenyl)-7H-pyrrolo-[2,3-d]pyrimidin-4-ylamine, m.p. 136.8-137.8° C.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated
  6. customto give an oil which
  7. customwas purified by flash column chromatography on silica
  8. customAppropriate fractions were collected
  9. customevaporated

Sources & evidence

ORD record
ord-b5fc4b5d592b4da4a2699470e4f40590
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

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