Ethyl Acetate → 2-Chloro-4-methyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

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Reaction Steps

A round-bottom flask was charged with 2-chloro-4-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (387 mg, 1.520 mmol) in THF (7.6 mL). To the resulting suspension was added lithium aluminum hydride in THF (1.0 M, 1975 μL, 1.975 mmol) dropwise at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred overnight. Ethyl acetate (˜1 mL) was subsequently added in portions at 0° C. Aqueous saturated NH4Cl (5 mL) was then added dropwise until bubbling stopped. The upper organic layer was decanted, concentrated, and then partitioned between brine and ethyl acetate. The murky bottom layer was extracted with ethyl acetate (3×) and the combined organic layers were dried over MgSO4, filtered, and concentrated. The product was triturated with ether/EtOAc and filtered under N2 to give the title compound as a yellow solid (264 mg, 72%). ESI-MS m/z [M+H]+ calc'd for C10H13ClN4O, 241.08; found 241.6.

Provenance & Evidence