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dimethyl-1,3-propanediimidate dihydrochloride[ No CAS ]
[ 75-09-2 ]
[ 584-08-7 ]
[ 2258-42-6 ]
[ 5270-94-0 ]
Yield
Reaction Conditions
Operation in experiment
With ammonia; sodium formate; In diethyl ether; water;
EXAMPLE 1 4,6-Dimethoxypyrimidine 5.0 g of dimethyl-1,3-propanediimidate dihydrochloride was added by vigorous stirring to a mixture of 25 ml of CH2 Cl2 and 25 ml of aqueous K2 CO3 solution (300 g of K2 CO3 /1 solution). After 5 minutes the organic phase was separated and the aqueous phase was extracted with 10 ml of Ch2 Cl2. The combined organic phases were dried on Na2 SO4 and filtered. A freshly prepared mixture of 2.5 g of formyl acetate [produced from acetyl choloride and sodium formate according to Muramatsu et al., Bull. Chem. Soc., Japan, 38, (1965), p. 244] in 2 ml of diethyl ether was added at 0 C. to the above solution of the diimidate and stirred for two hours at this temperature. A small amount of ammonia gas was introduced (or ethereal ammonia solution was added) so that the reaction mixture showed an approximately neutral reaction with moistened pH paper. After another hour of stirring at 0 C., 10 ml of water was added. The organic phase was separated, dried on Na2 SO4 and gently concentrated by evaporation. After distillation in a bulb tube furnace (product fraction: 110 C./16 mbar) the product was obtained as a colorless oil, which gradually solidified when allowed to stand. The yield of the product was: 2.4 g, which was 66.3 percent relative to the dihydrochloride used with a product content of 96 percent (GC).
With N-Bromosuccinimide; acetic anhydride; at 100℃; for 5.16h;
B. Preparation of 5-bromo-<strong>[5270-94-0]4,6-dimethoxypyrimidine</strong> To the solution of <strong>[5270-94-0]4,6-dimethoxypyrimidine</strong> (5 g, 35.7 mmol) in HOAc (20 mL) at room temperature under argon was added Ac2O (4.6 g, 44.6 mmol). The resulting solution was heated at 100 C. for 10 min and then NBS (7.9 g, 44.6 mmol) was added. Heating was continued at 100 C. for 5 h. Analysis by HPLC/MS indicated that the reaction was complete. After the reaction mixture was cooled to room temperature, water (50 mL) was added. The resulting precipitate was collected by filtration and further washed with water (15 mL*3), then dried under vacuum. The title compound (7.5 g) was obtained as a white solid. 1H NMR (CDCl3): delta 4.05 (s, 6H), 8.32 (s, 1H). 13C NMR (CDCl3): delta 55.2, 89.0, 154.9, 166.8.
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