Cl.C(OC1C=CC(C(N)=N)=CC=1)CCCC.C(OC(=O)C(=COCC)C#N)C.CC[O-].[Na+].[OH-].[Na+].[C:35]([C:37]1[C:38](O)=[N:39][C:40]([C:43]2[CH:48]=[CH:47][C:46]([O:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])=[CH:45][CH:44]=2)=[N:41][CH:42]=1)#[N:36].P(Cl)(Cl)([Cl:58])=O>C(O)C>[Cl:58][C:38]1[C:37]([C:35]#[N:36])=[CH:42][N:41]=[C:40]([C:43]2[CH:48]=[CH:47][C:46]([O:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])=[CH:45][CH:44]=2)[N:39]=1
The 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-pentyloxybenzamidine 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-pentyloxyphenyl)-pyrimidine (melting point 213.5°-215.5° C) is treated with phosphorus oxychloride to give 4-chloro-5-cyano-2-(4-n-pentyloxyphenyl)-pyrimidine having a melting point of 140.5°-142.0° C.
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