4-Chloro-2-methyl-6-phenylpyrimidine

In 4-chloro-2-methyl-6-phenylpyrimidine-5-carbonitrile, the reactivity of the chloro substituent allows the introduction of side chains which will cyclize with the adjacent nitrile function. Thus, cyanoacetamide yields 5-amino-2-methyl-7-oxo-7,8-dihydro-4-phenyipyrido[2,3-[Pg.110]

Other workers confirmed the above results but did not isolate any of the 4-nitrophenyl product. The nitration of 5-bromo and 5-chloro-2-phenylpyrimidine was also shown to yield the ortho and meta products (in the ratio of about 3 7) with no para isomer being observed (80H1989). Further work has indicated that 5-nitro-2-phenylpyrimidine undergoes nitration in mixed acid at 0°C to give a similar mixture of ortho and meta products (1 7) with no para isomer, whereas 6-methyl-2-phenylpyrimidin-4-one (72) forms only a 3-nitro phenyl product (91UP1). 

Amino-4-chloro-2-phenylpyrimidine (62) reacts with potassium amide in liquid ammonia to form 4-cyano-2-phenylimidazole (63) 4-chloro-5-methyl-2-phenylpyrimidine (64) gives 4-ethynyl-2-phenylimidazole (65) under the same conditions.These results are somewhat surprising in... 

Treatment of 5-acetyl-4-chloro-6-methyl-2-phenylpyrimidine (38, R1 = Ph R2 = Me) with urea leads to the corresponding pyrimido[4,5-d]pyrimidine 39 (R1 = Ph, R2 = Me). On the other hand, the reaction with thiourea affords not the expected 4,5-dimethyl-7-phenylpyrimido[4,5-t/]pyrimidine-2-thiol, but instead 5-acetyl-6-methyl-2-phenylpyrimidine-4-thiol.116... 

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