Benzoyl chloride, 3-nitro- → (4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-nitro-phenyl)-methanone

HRID 916754Notes

Reaction equation

HRID 916754 reaction equation
[Li]CCCC.Br[C:7]1[C:15]2[C:14]([Cl:16])=[N:13][CH:12]=[N:11][C:10]=2[N:9]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:8]=1.[N+:22]([C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=[O:29])([O-:24])=[O:23]>C1COCC1>[Cl:16][C:14]1[C:15]2[C:7]([C:28]([C:27]3[CH:31]=[CH:32][CH:33]=[C:25]([N+:22]([O-:24])=[O:23])[CH:26]=3)=[O:29])=[CH:8][N:9]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[C:10]=2[N:11]=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 8495Benzoyl chloride, 3-nitro-HCID 865964995-Bromo-4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidineHCID 178418339Butyllithium

Product 1

HCID 86760547(4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-nitro-phenyl)-methanoneYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-BuLi (22 mL, 2.5 M in Hexane, 55.0 mmol) was added dropwise to a solution of 5-Bromo-4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine (15.0 g, 50.0 mmol) in THF (200 mL) at −78° C. After 1 h the resulting solution was added via cannula to a solution of 3-Nitrobenzoyl Chloride in THF (100 mL) at −78° C. After 30 min the reaction was quenched with saturated aqueous NH4Cl and warmed to room temperature. The layers were separated and the aqueous layer was extracted with EtOAc (1×200 mL). The THF was concentrated off under reduced pressure and the resulting organic layer was diluted with EtOAc. The organic layer was washed with 1N NaOH (2×) and water (1×) then dried over Na2SO4 and concentrated. Recrystallization from EtOAc afforded the title compound as a white solid (12.1 g, 65%). MS: 371.2/373.1 (MH+); HPLC Rf: 6.59 min. (HPLC method 4).

Workup

  1. customAfter 30 min the reaction was quenched with saturated aqueous NH4Cl
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (1×200 mL)
  4. concentrationThe THF was concentrated off under reduced pressure
  5. additionthe resulting organic layer was diluted with EtOAc
  6. washThe organic layer was washed with 1N NaOH (2×) and water (1×)
  7. dry with materialthen dried over Na2SO4
  8. concentrationconcentrated
  9. customRecrystallization from EtOAc

Sources & evidence

ORD record
ord-08f7ad28acb842639ecc4276fa35b3ca
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

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