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

HRID 1192353Notes

Reaction equation

HRID 1192353 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.C1C(=O)N([Br:18])C(=O)C1>>[Br:18][C:10]1[C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=2[NH:8][CH:9]=1

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 53807105-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidineYield 80.7%

Procedure

To a suspension of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (2.5 g, 16 mmol) in CDCl3 (65 mL) was added NBS (2.9 g, 16 mmol) and the reaction mixture stirred and heated at reflux for 2.5 hours. The mixture was cooled to room temperature, the solids isolated by vacuum filtration, rinsed with cold CHCl3 and air dried to give 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (3.0 g, 79%.) LCMS (APCI+) m/z 232 and 234 [M+H]+; Rt: 2.32 min. 1H NMR (DMSO-d6, 400 MHz) δ 12.98 (1H, br. s), 8.63 (1H, s), 7.96 (1H, s.)

Workup

  1. temperatureheated
  2. temperatureat reflux for 2.5 hours
  3. customthe solids isolated by vacuum filtration
  4. washrinsed with cold CHCl3 and air
  5. customdried

Sources & evidence

ORD record
ord-5a7fd230c3f04c6c98de6690135e6a99
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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