Lithium hydride → 2-[N-(4-chlorophenyl)-N-(3-methoxybenzyl)amino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one

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The reaction procedure of Example 11 was followed except that 2.681 g (9.25 mmol) of 2-(4-chloroanilino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one, 162 mg of lithium hydride, 1.50 g of 3-methoxybenzyl chloride and 40 ml of DMF were used. The resulting residue was then purified through silica gel column chromatography (eluant: chloroform). As a result, 2.288 of 2-[N-(4-chlorophenylimino)-2,3-dihydro-4H-3-(3-methoxybenzyl)pyrido[3,2-e]-1,3-thiazin-4-one (recrystallized from ethanol) was obtained as a low polarity substance, and 843 mg of 2-[N-(4-chlorophenyl)-N-(3-methoxybenzyl)amino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one (recrystallized from a mixture of ethyl acetate and diisopropyl ether) was obtained as a high polarity substance.

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