Triacetoxyperiodinane → 5-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)picolinaldehyde

Participants

Reaction Conditions

Reaction Steps

To a 100 ml three necked round bottom flask, 1-(2-(6-(hydroxymethyl)pyridin-3-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one (0.32 g, 0.000702 mole) was taken in CH2Cl2 (20 ml) and cooled to 0° C. Dess Martin's reagent (1.11 g, 0.00245 mole) was added at 0° C. and the reaction was warmed to room temperature and stirred for 2 hrs under nitrogen atmosphere. After completion of the reaction, the reaction mixture was filtered through celite bed and washed with CH2Cl2. Filtrate was washed with water. Organic layers were combined, dried over Na2SO4, filtered and concentrated to afford crude product which was purified using column purification by eluting with 25-30% ethyl acetate in hexanes to yield 0.173 g of 5-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-2-yl-amino)-picolinaldehyde.

Provenance & Evidence