Ethyl 2-formyl-3-(3-methoxyphenyl)propionate → 2-Nitroamino-5-(3-methoxybenzyl)-4-pyrimidone

반응식

[CH:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)[C:4](OCC)=O)=[O:2].C[O-].[Na+].[N+:21]([NH:24][C:25]([NH2:27])=[NH:26])([O-:23])=[O:22]>CO>[N+:21]([NH:24][C:25]1[NH:27][C:1](=[O:2])[C:3]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)=[CH:4][N:26]=1)([O-:23])=[O:22]

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실험 절차

Ethyl 2-formyl-3-(3-methoxyphenyl)propionate (10 g) was added dropwise to a stirred and boiling mixture of sodium methoxide (from 1.15 g sodium) and nitroguanidine (25% wet, 5.5 g) in methanol (250 ml) and the mixture was heated under reflux for 20 hours and evaporated to dryness. The residue was dissolved in water (100 ml), the solution was extracted with ether and the aqueous phase was adjusted to pH 4: the solid which separated was recrystallized from ethanol to give 2-nitroamino-5-(3-methoxybenzyl)-4-pyrimidone (3.41 g, 29%), m.p 178°-9°.