Sodium Bicarbonate → 4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a 100 ml three necked round bottom flask 1-(2-(4-(hydroxymethyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one (2.3 g, 0.0051 mole) was taken in CH2Cl2 (25 ml). The reaction mixture was cooled to 5° C. and PCC (4.84 g, 0.0225 mole) was added at the same temperature under nitrogen atmosphere. The reaction mixture was warmed up to RT and then stirred for 2 hr. After completion of the reaction, the reaction mixture was poured into saturated NaHCO3 solution (50 ml) under stifling at 10° C. and the aq. layer was extracted with CH2Cl2. The combined organic layer was dried over Na2SO4, filtered and concentrated to afford crude product which was purified using column purification by eluting the compound with 15-20% ethyl acetate in hexanes to yield 1.7 g of 4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde.

Provenance & Evidence