5-Pyrimidinecarbonitrile

Amino-2,6-bis(cyanomethyl)-5-Pyrimidinecarbonitrile is formed as a byproduct in a yield of preparative interest, b.p.. Boiling point. 

AND 2-MERCAPTO-4-HYDRO XY-5-CYANOPYRIMIDINE (5-Pyrimidinecarbonitrile, 4-hydroxy-2-mercapto-,)... 

A soln. of N -cyano-N-(2-cyanoethyl)acetamidine in abs. tetrahydrofuran added dropwise to a vigorously stirred refluxing soln. of Na-N-methylanilide (prepared from Na, N-methylaniline, and monomeric stabilized styrene) in the same solvent, and stirring continued 2 hrs. at room temp. 4-amino-2-methyl-l,6 dihydro-5-pyrimidinecarbonitrile. Y 77%. A. Edenhofer, H. Spiegelberg, and W. E. Ober-hansli, Helv. 58, 1230 (1975) s. a. M.S. Newman et al., J. Org. Chem. 40, 2863 (1975) 4-aminoimidazoles with ethanolic Na-ethoxide (s. Synth. Meth. 18, 819) cf. A. Edenhofer, Helv. 58, 2192 (1975). 

Knoevenagel condensation between the aldehyde (1) and malononitrile (16) to form cyanoolefins (40), followed by a Michael addition with amidine (38), cycloaddition, isomerization, and aromatization to afford the 4-amino-5-pyrimidinecarbonitriles (39) (Figure 9.2). 

Pyrimidine-5-carbonitrile, 4-amino-6-methyl-synthesis, 3, 114 Pyrimidinecarbonitriles alcoholysis, 3, 83 aminolysis, 3, 83 hydrolysis, 3, 83, 127 oxides... 

Amino-7-phenylpyrimido[4,5- (]pyrimidine-2,4-diol (22) can be obtained by reacting 4,6-diamino-2-phenylpyrimidine-5-carboxamidc (21) with urea.110 The amide is prepared by hydrolysis of the corresponding pyrimidinecarbonitrile.109... 

Coterdn JM, Catterick D, Castro J, Chaparro MJ, Diaz B, Fernandez E, Ferrer S, Gamo FJ, Gordo M, Gut J, de las Heras L, Legac J, Marco M, Miguel J, Munoz V, Porras E, de la Rosa JC, Ruiz JR, Sandoval E, Ventosa P, Rosenthal PJ, Fiandor JM (2010) Falcipain inhibitors optimization studies of the 2-pyrimidinecarbonitrile lead series. J Med Chem 53 6129-6152... 

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