Selectfluor → 2,4-Dichloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine

HRID 2281427Notes

Reaction equation

HRID 2281427 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[B-](F)(F)(F)[F:13].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CC#N.CC(O)=O>[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[C:10]([F:13])=[CH:9][NH:8][C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 2724933SelectfluorHCID 141168712,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 594420712,4-Dichloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidineYield 22.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (200 mg, 1.06 mmol) and SelectFluor (560 mg, 1.58 mmol) in CH3CN (5 mL) and HOAc (1 mL) was stirred at 70° C. for 18 h. The mixture was then concentrated in vacuo. The residue was purified by HPLC to give 2,4-dichloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (50 mg).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-a1f8d02557bb45978cf9541983ebec41
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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