Acetic Acid → 1-[2-[3-(5,6-Dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-ylmethyl)-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one

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Reaction Steps

To a solution of 3-[7-(2,2-Dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-benzaldehyde (0.150 g, 0.3428 mmol) and 5,6,7,8-Tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine (0.064 g, 0.514 mmol) in 1.2 mL of dichloroethane was added 1.2 mL acetic acid and 0.109 g of sodium triacetoxyborohydride (0.514 mmol). The reaction was stirred overnight at room temperature before quenching with saturated aqueous Na2CO3. The reaction mixture was extracted 3 times with ethyl acetate, combined organics dried over MgSO4, filtered and concentrated in vacuo. Silica gel chromatography (0→100% EtOAc/hexanes over 30 minutes, followed by a flush with 100% methanol) afforded 0.0744 g (40% yield) of 1-[2-[3-(5,6-Dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-ylmethyl)-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a white solid. MS (E/I): 546 (M+H)

Provenance & Evidence