Acetyl chloride → 1-(2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethanone

HRID 2189302Notes

Reaction equation

HRID 2189302 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[Cl:9][C:10]1[N:11]=[CH:12][C:13]2[CH:18]=[CH:17][N:16]([CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[C:14]=2[N:15]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:9][C:10]1[N:11]=[CH:12][C:13]2[C:18]([C:5](=[O:7])[CH3:6])=[CH:17][N:16]([CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[C:14]=2[N:15]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 866373422-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 866373431-(2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethanoneYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of aluminium chloride (400 mg, 2.99 mmol) and acetyl chloride (711 uL, 10 mmol) in dichloromethane (2 mL) is added 2-chloro-7-(cyclopentyl)-7H-pyrrolo[2,3-d]pyrimidine (221 mg, 1.0 mmol) in dichloromethane (5 mL), dropwise. After 20 minutes saturated aqueous sodium bicarbonate is added to pH 9-10 and the solution is extracted with dichloromethane. The organic phase is dried, anhydrous Na2SO4 and concentrated to obtain 1-(2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethanone (255 mg, 97%) as an off-white amorphous solid (97%). 1H-NMR and LCMS.

Workup

  1. extractionthe solution is extracted with dichloromethane
  2. customThe organic phase is dried
  3. concentrationanhydrous Na2SO4 and concentrated

Sources & evidence

ORD record
ord-7523e394e25448fb9bb3b856a09d5bac
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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