Sodium → 4,4,6-Trimethyl-3,4,5,6-tetrahydropyrimidine

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To a sample of 126 grams of 4,4,6-trimethyl-2,3,4,5-tetrahydropyrimidine in 300 cc. of methanol was added with stirring and cooling over a 2 hr. period 20.8 grams of sodium boronhydride. The mixture was allowed to stand for 17 hrs. The reaction mixture was extracted with chloroform and the chloroform removed under diminished pressure. The remaining product was distilled and the fraction b25 76.5°-77° C. was collected as 108 grams of 4,4,6-trimethyl hexahydropyrimidine. Anal. Calc.ed for C7H16N2 : N, 21.85. Found: N, 21.6 Nuclear magnetic resonance spectrum, solvent CDCl3, δ in ppm; 3.82 s, 2H; 2.87 m, 1H; 1.42 & 1.65, 2d's, 2H; 1.02 d, 3H; 1.08 & 1.13 2s's, 6H; 1.67 s, 2H exchangeable with D2O. A sample of 12.8 grams of 4,4,6-trimethylhexahydropyrimidine and 0.5 grams of 60% nickel catalyst on kieselguhr was heated for 8 hrs. at 185°-187° C. During this time the theoretial amount of hydrogen gas was evolved.

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