2-Amino-3-cyano- 2-

Deshmukh MB, Salunkhe SM, Patil DR, Anbhule PV (2009) A novel and efficient one step synthesis of 2-amino-5-cyano-6-hydroxy-4-aryl pyrimidines and their anti-bacterial activity. Eur J Med Chem 44 2651-2654... 

A mixture of triethyl orthoacetate (20 mL), Ac O (20 mL), and 2-amino-5-cyano-6-methoxynicotinamide (0.5 g, 2.6 mmol) was heated at reflux for 2 h. The mixture was cooled to rt and 50% aq F.tOH was added. The precipitate was washed with H20 and dissolved in 1 M KOH (20 mL). The solution was filtered and acidified with HOAc to give a white solid yield 0.4 g (72 %). An analytical sample was recrystallized (DMF) to give colorless flakes which decomposed at 276-281 C. 

Amino-l,3-oxazin-6-ones can be isolated as crystalline compounds and, for example, the structures of 2-amino-5-cyano-4-methylthio-l,3-oxazin-6-one (12) <85HCA1155>, 5-ethoxycarbonyl-2-(A,A-dimethylamino)-4-phenyl-l,3-oxazin-6-one (13), and 4-ethoxycarbonyl-2-(A7,A-dimethyl-... 

The potassium salt of tetracyanopropene (MI-15, M = K) gives 2-amino-5-cyano-6-hydroxy-3-pyridinecarboxamide (XII-16, R = H) when heated in aqueous aDali In aqueous alcohols, MI-15 forms 6-alkoxy-2-araino-3,5-di-cyanopyridines (Xn-17 R =H, R = CH3,C2Hs) or6-alkoxy-2-amino-5-cyano-... 

Amino-l,3-dicyano-2-methylpenta-l,3-diene refluxed 20 min. with KOH in ethanol 2-amino-5-cyano-4,6-lutidine. Y almost 100. E. Bullock and B. Gregory, Gan. J. Ghem. 43, 332 (1965). 

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