Cl.[CH2:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=N)=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].C(OC(=O)C(=COCC)C#N)C.CC[O-].[Na+].[OH-].[Na+].C(C1C(O)=[N:37][C:38]([C:41]2[CH:46]=[CH:45]C(CCCC)=C[CH:42]=2)=NC=1)#N.P(Cl)(Cl)([Cl:54])=O>C(O)C>[Cl:54][C:46]1[C:41]([C:38]#[N:37])=[CH:42][N:12]=[C:10]([C:9]2[CH:8]=[CH:7][C:6]([CH2:2][CH2:3][CH2:4][CH3:5])=[CH:14][CH:13]=2)[CH:45]=1The starting material can be obtained according to the procedure of A. R. Todd and F. Bergel, J. Chem. Soc. 1937, 365 by reaction of p-n-butylbenzamidine hydrochloride with α -ethoxymethylene- α -cyanoacetic acid ethyl ester and sodium ethylate in ethanol and then with sodium hydroxide solution. The resulting 5-cyano-4-hydroxy-2-(4-n-butylphenyl)-pyrimidine (melting point 230.3°-231.3° C) is treated with phosphorus oxychloride to give 4-chloro-5-cyano-2-(4-n-butylphenyl)-pyridine having a melting point of 106.8°-107.0° C.
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