Methyl morpholine oxide → 2-(4-Chloro-6-(pyridin-2-yl)pyrimidin-5-yl)acetaldehyde

Participants

Reaction Steps

To a stirred solution of 5-allyl-4-chloro-6-(pyridin-2-yl)pyrimidine (1 g) in dry dioxane (10 mL), N-methyl morpholine N-oxide (0.75 g) and osmium tetroxide (0.35 mL, 25% solution in water) were added. The reaction mixture was stirred at room temperature for 2 hours before being quenched by solid sodium bisulphate. The reaction mixture was filtered through celite bed and the celite bed was washed with dioxane (5 mL). The combined filtrate was taken into a 100 mL three necked round bottom flask and sodium metaperiodate (2.3 g, in 5 mL water) was added. The reaction mixture was stirred at room temperature for 3 hours and then diluted with water (30 mL). Aqueous layer was extracted with dichloromethane (2×25 mL). The combined organic layer was washed with brine (50 mL) and dried over anhydrous Na2SO4. Evaporation of solvents under reduced pressure gave crude 2-(4-chloro-6-(pyridin-2-yl)pyrimidin-5-yl)acetaldehyde (0.7 g) which was used as was. 1H NMR (DMSO-d6): δ 4.12 (s, 2H), 7.53-7.55 (m, 1H), 7.88-8.01 (m, 2H), 8.66-8.69 (d, 1H), 8.97 (s, 1H), 9.79 (s, 1H).

Provenance & Evidence