Triacetoxyperiodinane → 1-(2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)ethanone
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]=1Participants
4
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.