Hydrogen Peroxide → 2-Chloro-7-(2,3-dihydroxy-propyl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one

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Reaction Conditions

Reaction Steps

A mixture of 7-allyl-2-chloro-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (Intermediate E, 40.8 mg, 195 μmol), 4-methylmorpholine N-oxide (11.4 mg, 97.3 μmol), and potassium osmate(VI) dihydrate (717 μg, 1.95 μmol) in tert-butanol (730 μL) and water (243 μL) cooled to 0° C. was treated with a 50% aqueous hydrogen peroxide solution (20 μL, 292 μmol). The reaction was allowed to warm to room temperature, where it stirred overnight. At this time, the reaction was diluted with methanol and absorbed onto Celite®. Flash chromatography (4 g silica gel column, 2-8% methanol/methylene chloride) afforded 2-chloro-7-(2,3-dihydroxy-propyl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one as an off-white solid (16.4 mg, 34.6%). 1H NMR (300 MHz, DMSO-d6) δ ppm 3.57 (s, 1H) 3.80 (d, J=9.42 Hz, 1H) 3.85-3.99 (m, 1H) 4.14-4.29 (m, 1H) 4.75 (t, J=5.75 Hz, 1H) 4.98 (d, J=5.46 Hz, 1H) 6.46 (d, J=3.39 Hz, 1H) 7.12 (d, J=3.20 Hz, 1H) 12.80 (s, 1H). LC-MS calcd. for C9H11ClN3O3 [(M+H)+] 244, obsd. 243.9.

Provenance & Evidence