Sodium sulfate decahydrate → HCID 57786342, compound

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (106 mg, 2.79 mmol) in tetrahydrofuran (3.5 mL) was added a solution of methyl 9-bromo-1-(4-methoxy-2-methylphenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (301 mg, 0.700 mmol) in tetrahydrofuran (3.5 mL) at 0° C., and the resultant mixture was stirred at 0° C. for 10 min. After sodium sulfate decahydrate (1 g) was added at 0° C., the resultant mixture was filtered and concentrated in vacuo. To a solution of the residue in acetonitrile (7 mL) and dimethylsulfoxide (1.4 mL) was added Dess-Martin reagent (356 mg, 0.839 mmol) at room temperature. The resultant mixture was stirred at room temperature for 30 min and diluted with aqueous sodium bicarbonate and aqueous sodium thiosulfate. The resultant mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture to give the title compound as a yellow solid (249 mg, 0.622 mmol, 89%).

Provenance & Evidence