N-bromobutanimide → 4-amino-6-bromo-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 51493

Reaction equation

HRID 51493 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Br:24]N1C(=O)CCC1=O>CC(N(C)C)=O.ClCCl>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][CH:16]=3)=[C:9]([Br:24])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 120422345-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Product 1

HCID 227362094-amino-6-bromo-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine (302 mg) was dissolved in dimethylacetamide (10 ml) and dichloromethane (50 ml) and then treated with N-bromosuccinimide (178 mg) in dichloromethane (10 ml). The mixture was left stirring ambient temperature for 16 hours. The mixture was evaporated under reduced pressure and the residue was triturated with water to give a solid which was collected by filtration and dried to give 4-amino-6-bromo-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine, m.p. 282-283° C.

Workup

  1. waitThe mixture was left
  2. customThe mixture was evaporated under reduced pressure
  3. customthe residue was triturated with water
  4. customto give a solid which
  5. filtrationwas collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-735dbb4832524a4697bc80fb09f17b0a
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Linked notes

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