N-bromobutanimide → 5-Bromo-4-chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 736333Notes

Reaction equation

HRID 736333 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:11]2[CH:18]=[CH:17][N:16]([CH:19]([CH3:21])[CH3:20])[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]([CH:19]([CH3:21])[CH3:20])[CH:17]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 722073574-Chloro-7-isopropyl-7H-pyrrolo[2,3-D]pyrimidine

Product 1

HCID 457894285-Bromo-4-chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidineYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Bromosuccinimide (165 g, 926 mmol) was added to a solution of 4-Chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine (151 g, 772 mmol) in CH2Cl2 (1 L). After 12 h the reaction was quenched with saturated aqueous NaHCO3 (500 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (2×500 mL). The combined organic layers were washed with water (3×500 mL) and brine (1×500 mL), dried (Na2SO4), filtered, and concentrated in vacuo to afford the title compound as a white solid (198 g, 94%). MS: 275.5 (MH+); HPLC Rf: 5.99 min. (HPLC method 4).

Workup

  1. customAfter 12 h the reaction was quenched with saturated aqueous NaHCO3 (500 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (2×500 mL)
  4. washThe combined organic layers were washed with water (3×500 mL) and brine (1×500 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-900da7598958402d83641fdd38cc8f7c
Source dataset
uspto-grants-2009_09
Patent number
US07595325B2

Reaction notes

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