反应详情

To a stirred solution of 0.87 g (3.2 mmol) of crude 6-carboxy-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone, 0.32 g (3.9 mmol) of dimethylamine hydrochloride and 2 mL of pyridine in 10 mL of THF was added 0.74 g (3.6 mmol) of solid N,N'-dicyclohexylcarbodiimide. The mixture was stirred at room temperature for 4 days and filtered to remove insoluble material. The filtrate was diluted with 150 mL of ethyl acetate, washed with 50 mL of 5% aqueous HCl and 50 mL of saturated aqueous sodium bicarbonate and dried over MgSO4. Removal of the solvent left 0.40 g of crude product which was purified by flash chromatography on a 30 g column of silica gel, eluted with 60, 80 and 100% ethyl acetate in hexanes to furnish 0.30 g (32%) of 6-dimethylaminocarbonyl-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (compound 19), mp 137°-140° C. 1H-NMR (CDCl3) δ2.15(3H,s), 2.40(1H,t), 3.00(3H,s), 3.10(3H,s), 4.65(2H,d), 7.55(3H,m), 7.70 (2H,m).

1. filtrationfiltered
2. customto remove insoluble material
3. additionThe filtrate was diluted with 150 mL of ethyl acetate
4. washwashed with 50 mL of 5% aqueous HCl and 50 mL of saturated aqueous sodium bicarbonate
5. dry with materialdried over MgSO4
6. customRemoval of the solvent
7. waitleft 0.40 g of crude product which
8. customwas purified by flash chromatography on a 30 g column of silica gel
9. washeluted with 60, 80 and 100% ethyl acetate in hexanes