Cyanoacetic acid → HCID 15136415, compound

Participants

Reaction Steps

α-Amino-p-tolunitrile (prepared from α-bromotolunitrile in a modification of the method described by J.H. Short and T.D. Darby, J. Med. Chem., 10 (5), 833, 1967) was treated first with methyl isocyanate followed by cyanoacetic acid according to the method of V. Papesch and E. F. Schroeder (J. Org. Chem., 1951, 16, 1879) to yield 4-[(6-amino-1,2,3,4-tetrahydro-3-methyl-2,4-dioxo-1-pyrimidinyl)methyl]benzonitrile, which was then nitrosated, reduced, and condensed with 4-formylcinnamic acid following an analogous procedure to that of Example 3 to give the title compound as a yellow solid with a melting point greater than 350° C. Analysis for (C23H17N5O4): C, 64.63; H, 4.01; N, 16.38. Found: C, 64.58; H, 4.06; N, 16.36.

Provenance & Evidence