Ammonium formate → 6-(4-oxo-2-phenoxymethyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-5-yl)-3',4',5',6'-tetrahydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

10% Palladium on charcoal (11 mg, 0.01 mmol) was added to a stirred suspension of 6-(4-oxo-2-phenoxymethyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-5-yl)-3′,6′-dihydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (51 mg, 0.10 mmol) and ammonium formate (38 mg, 0.61 mmol) in MeOH (0.5 mL) in a sealed tube and under nitrogen. The mixture was stirred at 80° C. for 30 minutes. The mixture was filtered through a pad of diatomaceous earth and washed with DCM. The filtrate was treated with brine and extracted with more DCM. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 50/50). The desired fractions were collected and the solvents evaporated in vacuo to yield 6-(4-oxo-2-phenoxymethyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-5-yl)-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (44 mg, 86% yield) as a yellow oil.

Provenance & Evidence