Ammonium formate → 3-fluoro-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-phenylamine

HRID 1011288Notes

Reaction equation

HRID 1011288 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[C:6]2[CH:13]=[CH:12][NH:11][C:7]=2[N:8]=[CH:9][N:10]=1.C([O-])=O.[NH4+]>C(O)C>[F:1][C:2]1[CH:17]=[C:16]([NH2:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[C:6]2[CH:13]=[CH:12][NH:11][C:7]=2[N:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 589380144-(2-fluoro-4-nitro-phenoxy)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 589380223-fluoro-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-phenylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a round bottom flask equipped with a magnetic stir bar was added 4-(2-fluoro-4-nitro-phenoxy)-7H-pyrrolo[2,3-d]pyrimidine (0.5 g, 2.0 mmol, 1.0 eq.), 5% PtS (20% by weight, 120 mg) ammonium formate (451 mg, 6 eq), and ethanol (20 ml). The reaction mixture was heated at reflux with stirring for 30 min upon which the reaction was filtered hot through celite. Removal of the ethanol was followed by the addition of 1N HCl, which was further washed twice with DCM (50 ml). The aqueous layer was basified and extracted with DCM. The organic layer was then washed twice with brine (50 ml) and dried over sodium sulfate. After removal of solvent in vacuo, 3-fluoro-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-phenylamine as a brownish solid was obtained (0.281 g, 63%). MS (ESI) for C12H9FN4O: 244 (MH+).

Workup

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux
  4. filtrationwas filtered hot through celite
  5. customRemoval of the ethanol
  6. additionwas followed by the addition of 1N HCl, which
  7. washwas further washed twice with DCM (50 ml)
  8. extractionextracted with DCM
  9. washThe organic layer was then washed twice with brine (50 ml)
  10. dry with materialdried over sodium sulfate
  11. customAfter removal of solvent in vacuo

Sources & evidence

ORD record
ord-ae113998970b455f9f71905727dbe02e
Source dataset
uspto-grants-2011_07
Patent number
US07977345B2

Reaction notes

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