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

HRID 1396596Notes

Reaction equation

HRID 1396596 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[B-](F)(F)(F)[F:12].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C.CC(O)=O>[Cl:1][C:2]1[C:3]2[C:10]([F:12])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 2724933SelectfluorHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (F-1) (5.01 g, 32.6 mmol, 1 eq) and selectfluor (17.32 g, 48.9 mmol, 1.5 eq) are dissolved in a mixture of anhydrous acetonitrile (250 mL) and AcOH (50 mL). The resulting mixture is stirred at 70° C. under argon for 16 h. The mixture is concentrated in vacuo. The residue is dissolved in a mixture of DCM-ethyl acetate (v/v=1/1, 50 mL) and filtered through celite. The filtrate is concentrated in vacuo and the residue is purified by flash chromatography on silica gel (0-0.7% MeOH-DCM) to afford the product, 4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (F-2).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. dissolutionThe residue is dissolved in a mixture of DCM-ethyl acetate (v/v=1/1, 50 mL)
  3. filtrationfiltered through celite
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe residue is purified by flash chromatography on silica gel (0-0.7% MeOH-DCM)

Sources & evidence

ORD record
ord-e2e9fc930cbe451d805f1cbd49841687
Source dataset
uspto-grants-2014_12
Patent number
US08901133B2

Reaction notes

Loading…