Propanal → HCID 67598026, compound

Participants

Reaction Conditions

Reaction Steps

650 mg (1.67 mmol) of 1-(8-ethylamino-5-hydroxy-5-methyl-6-octynyl)-3-methyl-7-propylxanthine from Example 23 were dissolved in 30 ml of ethanol. After cooling to -78° C., 602 μl (8.34 mmol) of propionaldehyde were added and, after warming to 0° C., 105 mg (1.67 mmol) of sodium cyanoborohydride were added. In order to complete the reaction, a spatula tip of sodium cyanoborohydride was added after 2 hours, and a further 602 μl (8.34 mmol) of propionaldehyde and 105 mg (1.67 mmol) of sodium cyanoborohydride were added after 3 hours. After the reaction was complete, the reaction mixture was concentrated in a rotary evaporator under reduced pressure, sodium bicarbonate solution was added to the residue, the aqueous phase was extracted with dichloromethane, the combined extracts were dried with magnesium sulfate, the desiccant was filtered off, and the filtrate was concentrated under reduced pressure in a rotary evaporator. The crude product was purified by flash chromatography with the mobile phase mixture dichloromethane/methane/saturated ammonia solution=19/1/0.02.

Provenance & Evidence