Sodium Sulfite → HCID 86667336, compound

Participants

Reaction Steps

To a stirred solution of 7-allyl-2-chloro-5,7-dimethyl-4-morpholino-5H-pyrrolo[3,2-d]pyrimidin-6(7H)-one (80.0 mg, 0.25 mmol) in anhydrous THF (3.0 m) and water (1.0 mL) cooled to 0° C. was added N-methylmorpholine N-oxide (34.8 mg, 0.29 mmol), followed by 2.5% osmium tetraoxide in tent-butanol. (0.033 mL, 0.025 mmol). The reaction mixture was stirred at ambient temperature under N2 for 16 h. Sodium sulfite (312.4 mg, 2.48 mmol) was then added, and the reaction mixture was stirred at RT for 20 min. The reaction mixture was diluted with water and then extracted with ethyl acetate (2×). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude intermediate was then diluted with anhydrous THF (3.0 mL) and water (1.0). Sodium periodate (79.5 mg, 0.372 mmol) was added, and the reaction mixture was sonicated for 1 minute and then stirred at RT for 2 days. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 80.4 mg (99%) of 2-(2-chloro-5,7-dimethyl-4-morpholino-6-oxo-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)acetaldehyde. MS(ESI) m/z: 325.1 [M+1]−.

Provenance & Evidence