Methanamine, N-methoxy-, hydrochloride (1:1) → 4-((tert-Butyldimethylsilyl)oxy)-3-((5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)methyl)-N-methoxy-N-methylbutanamide

Participants

Reaction Steps

T3P® (2.62 mL, 4.5 mmol) was added to a suspension of 4-((tert-butyldimethylsilyl)oxy)-3-((5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)methyl)butanoic acid (1.13 g, 2.2 mmol), DIPEA (2.16 mL, 12.3 mmol) and N,O-dimethylhydroxylamine hydrochloride (263 mg, 2.7 mmol) in DMF (8 mL) at 0° C. The mixture was stirred at room temperature for 30 minutes. The reaction was diluted with ethyl acetate (40 mL) and was washed with water (1×20 mL), 1M HCl(aq) (1×20 mL) and saturated NaHCO3(aq) (1×20 mL). The organic phase was dried over magnesium sulfate and the solvent was removed under vacuum. Purification by chromatography on silica, eluting with 0-3% MeOH/DCM, afforded the title compound.

Provenance & Evidence