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

HRID 920669

Reaction equation

HRID 920669 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C1C(=O)N([Br:18])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Br:18][C:8]1[C:6]2[N:7]=[C:2]([Cl:1])[N:3]=[CH:4][C:5]=2[NH:10][CH:9]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 457899862-Chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 867311617-Bromo-2-chloro-5H-pyrrolo[3,2-d]pyrimidineYield 75.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-chloro-5H-pyrrolo[3,2-d]pyrimidine (1.54 g, 10 mmol) in DMF (10 mL) was added NBS (2.00 g, 11 mmol) at room temperature. The resulting solution was stirred for 1 h and diluted with EtOAc. The resulting solution was washed with a sat. aq. solution of NaHCO3, H2O and brine. The EtOAc layer was dried (Na2SO4), concentrated and purified by ISCO to provide the desired product (1.75 g, 75%). 1H NMR (400 MHz, CD3OD) δ 8.53 (s, 1H), 7.60 (s, 1H); MS m/z 234.0 [M+H]+.

Workup

  1. washThe resulting solution was washed with a sat. aq. solution of NaHCO3, H2O and brine
  2. dry with materialThe EtOAc layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by ISCO

Sources & evidence

ORD record
ord-15074791c24c4f36aac2fea6e8b49469
Source dataset
uspto-grants-2016_03
Patent number
US09273056B2

Linked notes

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