Water → HCID 89630046, compound

HRID 882153Notes

Reaction equation

HRID 882153 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]3[CH:18]=[CH:17][NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C1C(=O)N([Br:26])C(=O)C1.O>CN(C=O)C>[Br:26][C:18]1[C:11]2[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[N:15][CH:14]=[N:13][C:12]=2[NH:16][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 89629882HCID 89629882, compound

Product 1

HCID 89630046HCID 89630046, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4-(3-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidine (12 g, 50 mmol) in DMF (167 mL) was added NBS (10.2 g, 57.4 mmol) and the mixture stirred for 30 minutes. Water (833 mL) was added which led to the precipitation of the desired product. The reaction mixture was allowed to stir for 15 minutes before being filtered and washed with 500 mL of water to give 5-bromo-4-(3-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidine. LRMS (ESI) calc'd for C12H8BrN4O2[M+H]+: 319, found 319.

Workup

  1. customled to the precipitation of the desired product
  2. stirringto stir for 15 minutes
  3. filtrationbefore being filtered
  4. washwashed with 500 mL of water

Sources & evidence

ORD record
ord-0bf404a3f5034a3a8917b537fbcb5ccd
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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