Malononitrile → 4-Amino-5-pyrimidinecarbonitrile

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Reaction Steps

Formamidine acetate (104.11 g., 1.00 mole) and malononitrile (33.03 g., 0.50 mole) are added to a solution of sodium ethoxide prepared from sodium (24.2 g., 1.05 mole) and absolute ethanol (750 ml.) in a nitrogen atmosphere. The mixture is stirred at room temperature for 48 hours. The off-white solid which separates is collected by filtration, washed with ice water then dried at 80° C./house vac. (ca. 200 mm.). The yield of product melting at greater than 340° C. (uncorr.) is 28.5 g. (47.0%). Recrystallization of this material from water (Darco G-60) affords cream-colored needles melting at 250° C. dec. (uncorr.) in a yield of 11.3 g. (18.8%).

Provenance & Evidence