N-bromobutanimide → HCID 69204850, compound

HRID 2053024Notes

Reaction equation

HRID 2053024 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[C:23]3[C:22]([NH2:24])=[N:21][CH:20]=[N:19][C:18]=3[NH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:25]N1C(=O)CCC1=O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[C:23]3[C:22]([NH2:24])=[N:21][CH:20]=[N:19][C:18]=3[NH:17][C:16]=2[Br:25])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 187928915-(3-(benzyloxy)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 69204850HCID 69204850, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 20 g (63.2 mmol) 5-(3-benzyloxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (see WO 97/28161) in 1 l dry N,N-dimethylformamide, 12.4 g (69.5 mmol) N-bromosuccinimide are added at ca. 10° C. Stirring was continued at ca. 10° C. for 30 min and overnight at RT. The precipitate formed is filtered off and washed thoroughly with N,N-dimethylformamide and hexane. After drying for 24 h at 30-35° C. under vacuum, the title compound is used in the next step without further purification. Additional material can be obtained from the mother liquor through chromatography on silicagel. Analytical HPLC: tR=10.07 min (Grad 1); ES-MS: m/eo=394.9 and 396.9; NMR (DMSO-d6): 12.55/s (NH); 8.06/s (1H), 7.25-7.5/several m's (6H), 7.07/“d” (1H); 7.03/s (1H); 6.98/“d” (1H); 5.5-6.0/b (NH2); 5.12/s (2H).

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. washwashed thoroughly with N,N-dimethylformamide and hexane
  4. customAfter drying for 24 h at 30-35° C. under vacuum
  5. customthe title compound is used in the next step without further purification
  6. customAdditional material can be obtained from the mother liquor through chromatography on silicagel

Sources & evidence

ORD record
ord-65bce323d5b2444db4c22b1c69fe55c8
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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