Triacetoxyperiodinane → 1-(2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)ethanone

HRID 2189327Notes

Reaction equation

HRID 2189327 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([CH:11]([OH:13])[CH3:12])[N:8]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:6]=2[N:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([C:11](=[O:13])[CH3:12])[N:8]([CH:14]([CH2:15][CH3:16])[CH2:17][CH3:18])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 735546611-(2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)ethanol

Product 1

HCID 735546581-(2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)ethanoneYield 109.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-ethanol (61 mg, 0.2 mmol) in CH2Cl2 (2 mL) is added Dess-Martin periodinane (242 mg, 0.5 mmol). The reaction mixture is stirred for 1 h, quenched with 10% NaS2O3:saturated NaHCO3 (1:1) aqueous solution, and extracted with CH2Cl2. The extracts are washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The residue is purified by flash chromatography (SiO2, EtOAc/Hexane 1:3) to afford 58 mg of 1-[2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-ethanone.

Workup

  1. customquenched with 10% NaS2O3
  2. extractionsaturated NaHCO3 (1:1) aqueous solution, and extracted with CH2Cl2
  3. washThe extracts are washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash chromatography (SiO2, EtOAc/Hexane 1:3)

Sources & evidence

ORD record
ord-d0b104fe8ec845cf86ae85f1f0c6d40c
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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