Nitric Acid → (4aS,5R,7aS)-2-Amino-7a-(2-fluoro-5-nitrophenyl)-3,5-dimethyl-4a,5,7,7a-tetrahydrofuro[3,4-d]pyrimidin-4(3H)-one

Participants

Reaction Steps

tert-Butyl ((4aS,5R,7aS)-7a-(2-fluorophenyl)-3,5-dimethyl-4-oxo-3,4,4a,5,7,7a-hexahydrofuro[3,4-d]pyrimidin-2-yl)carbamate (2.15 g, 5.7 mmol) was taken up in fuming nitric acid (5 ml) at RT—note exotherm. The dark brown solution was stirred at RT overnight and then at 50° C. for 24 h. The reaction was allowed to cool to RT. Ice (˜25 g) was added and then the mixture was basified with 50% aqueous NaOH with ice bath cooling. The pH was readjusted with saturated aqueous NH4Cl and then the mixture was extracted with DCM (×4). The combined extracts were dried (Na2SO4), filtered and evaporated to give the title compound (1.8 g, yellow foam). LCMS (Method A) Rt 3.00 min; ESI-MS: m/z 323 [M+H]+. This material was used without further manipulation.

Provenance & Evidence