N-bromobutanimide → 5-Bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine

HRID 2281422Notes

Reaction equation

HRID 2281422 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.C1C(=O)N([Br:19])C(=O)C1>C(Cl)Cl>[Br:19][C:10]1[C:5]2[C:4]([Cl:11])=[N:3][C:2]([Cl:1])=[N:7][C:6]=2[NH:8][CH:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 141168712,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 579904405-Bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidineYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (105 mg, 0.560 mmol) in CH2Cl2 (7 mL) at room temperature, NBS (109 mg, 0.610 mmol) was added. The mixture was stirred at room temperature for 18 h. CH2Cl2 was removed in vacuo. The residue was partitioned between water and EtOAc. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 5-bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (142 mg).

Workup

  1. customCH2Cl2 was removed in vacuo
  2. customThe residue was partitioned between water and EtOAc
  3. customThe organic phase was separated
  4. washwashed with 5% NaHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-45b6e93bce4e4bb3980280715d11828b
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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