Cyanoacetamide → 2-cyano-3-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)acrylamide

Participants

Reaction Steps

To a 50 ml three necked round bottom flask 4-(7-pivaloyl-5-((2-(trimethylsilyl)-ethoxy)-methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde (0.25 g, 0.0005 mole) and 2-cyanoacetamide (0.094 g, 0.0011 mole) was taken in ethanol (20 ml). To this reaction mixture, piperidine acetate (3.3 M solution in water) (1.0 ml) was added drop wise at RT. After completion of the addition, reaction mixture was refluxed for 2 hr. After completion of the reaction, the ethanol was distilled out and water was added to residue. The aq. layer was extracted with ethyl acetate, the organic layers were combined, dried over Na2SO4, filtered and concentrated to afford crude product. The crude compound was purified by triturated with n-pentane, pentane layer was decanted and solid was dried under vacuum to yield 0.25 g of 2-cyano-3-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)-methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)acrylamide.

Provenance & Evidence