Selectfluor → 4-Chloro-5-fluoro-7H-pyrrolo(2,3-d)pyrimidine

HRID 2252710Notes

Reaction equation

HRID 2252710 reaction equation
C[Sn](C)(C)[C:3]1[C:11]2[C:10]([Cl:12])=[N:9][CH:8]=[N:7][C:6]=2[NH:5][CH:4]=1.[F:15][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>CC#N>[F:15][C:3]1[C:11]2[C:10]([Cl:12])=[N:9][CH:8]=[N:7][C:6]=2[NH:5][CH:4]=1

Participants

4

Reactant 2

HCID 2724933Selectfluor2×HCID 114612365-(Trimethylstannyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 113212244-Chloro-5-fluoro-7H-pyrrolo(2,3-d)pyrimidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the compound from Step B (1.97 g, 6.20 mmol) in CH3CN (60 mL) was added [1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)] (SELECTFLUOR® fluorinating reagent) (2.40 g, 6.5 mmol) in one portion and the reaction mixture was stirred at room temperature for 7 h. The white precipitate was filtered off, and the filtrate was evaporated to dryness. The residue was purified over silica gel using ethyl acetate/hexane (3:7) as the eluent. Fractions containing the product were pooled and eveporated in vacuo to give the title compound as a colorless solid.

Workup

  1. filtrationThe white precipitate was filtered off
  2. customthe filtrate was evaporated to dryness
  3. customThe residue was purified over silica gel
  4. additionFractions containing the product

Sources & evidence

ORD record
ord-72b7a59eb3684225abb22ea91a3f91ee
Source dataset
uspto-grants-2008_01
Patent number
US07323453B2

Reaction notes

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