N-bromobutanimide → HCID 77520043, compound

HRID 736338Notes

Reaction equation

HRID 736338 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:11]2[CH:18]=[CH:17][N:16]([Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[C:12]=2[N:13]=[CH:14][N:15]=1>C(Cl)Cl>[Br:1][C:18]1[C:11]2[C:10]([Cl:9])=[N:15][CH:14]=[N:13][C:12]=2[N:16]([Si:19]([CH:23]([CH3:25])[CH3:24])([CH:26]([CH3:28])[CH3:27])[CH:20]([CH3:21])[CH3:22])[CH:17]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 77231601HCID 77231601, compound

Product 1

HCID 77520043HCID 77520043, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Bromosuccinimide (60.3 g, 338 mmol) was added to a solution of 4-Chloro-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidine (100 g, 323 mmol) in CH2Cl2 (1 L). After 12 h 15 the reaction was quenched with saturated aqueous NaHCO3 (500 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (4×500 mL). The combined organic layers were filtered through silica gel and concentrated in vacuo. Purification by flash column chromatography (ethyl acetate/hexanes 1:99) afforded the title compound as a clear solid (89.5 g, 72%). MS: 388.8/390.8 (MH+); HPLC Rf: 9.84 min. (HPLC method 4).

Workup

  1. customAfter 12 h 15 the reaction was quenched with saturated aqueous NaHCO3 (500 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (4×500 mL)
  4. filtrationThe combined organic layers were filtered through silica gel
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (ethyl acetate/hexanes 1:99)

Sources & evidence

ORD record
ord-a885f09f5b904e2ab7e3b0ae0d23cbe8
Source dataset
uspto-grants-2009_09
Patent number
US07595325B2

Reaction notes

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