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

HRID 916753Notes

Reaction equation

HRID 916753 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:11]2[CH:18]=[CH:17][N:16]([CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[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]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:17]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 5198484-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 865964995-Bromo-4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidineYield 61.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Bromosuccinimide (15.4 g, 86.8 mmol) was added to a solution of 4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine (15.4 g, 69.5 mmol) in CH2Cl2 (100 mL). After 12 h the reaction was quenched with saturated aqueous NaHCO3 (100 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (2×100 mL). The combined organic layers were dried over Na2SO4 and concentrated. Purification by flash column chromatography (hexanes/ethyl acetate 9:1) afforded the title compound as a white solid (12.8 g, 61%). MS: 300.1/302.0/304.1 (MH+); HPLC Rf: 6.68 min. (HPLC method 4).

Workup

  1. customAfter 12 h the reaction was quenched with saturated aqueous NaHCO3 (100 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (2×100 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (hexanes/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-62f10175679d43a29cbc6cfdbacce4bb
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

Loading…