Acetone → HCID 136247202, compound

Participants

Reaction Steps

A solution of 7-but-3-enyl-2-(4-trifluoromethyl-phenyl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (50.3 mg, 151 μmol) in acetone (1.2 mL) and water (0.4 mL) was treated with potassium permanganate (46.1 mg, 292 μmol). The reaction stirred at room temperature overnight. The reaction was filtered through a coarse sintered glass frit, rinsing with ethyl acetate. The filtrate was concentrated in vacuo and then partitioned between water (25 mL) and ethyl acetate (25 mL). The aqueous layer was back extracted with ethyl acetate (25 mL), and the combined organics were washed with a saturated aqueous sodium chloride solution (25 mL), dried over magnesium sulfate, filtered and rinsed with ethyl acetate, and concentrated in vacuo. Flash chromatography (24 g silica gel column, 1-10% methanol/methylene chloride) afforded 7-(3,4-dihydroxy-butyl)-2-(4-trifluoromethyl-phenyl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one as a white solid (6.9 mg, 12.4%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.72 (s, 1H) 1.85-2.15 (m, 1H) 3.10-3.53 (m, 3H) 4.09-4.45 (m, 2H) 4.48-4.62 (m, 1H) 4.72 (d, J=5.09 Hz, 1H) 6.53 (d, J=3.20 Hz, 1H) 7.12-7.34 (m, 1H) 7.90 (d, J=8.29 Hz, 2H) 8.34 (d, J=8.48 Hz, 2H) 12.3.1 (s, 1H). LC-MS calcd. for C17H17F3N3O3 [(M+H)+] 368, obsd. 368.0.

Provenance & Evidence