Реакция #1539

Уравнение реакции

benzamidine hydrochloride hydrate

sodium methoxide

diethyl ethylmalonate

→

5-ethyl-6-hydroxy-2-phenyl-4(3H)-pyrimidinone

Выход 51.0%

Растворители

methanol

methanol

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   Температураat reflux for 25 h
3. 3
   Другоеto remove the bulk of the methanol
4. 4
   workup.ADDITIONThe residue was diluted with 300 mL of water
5. 5
   ФильтрацияThe solid precipitate was collected by filtration
6. 6
   Другоеdried under vacuum at 50° C.

Методика

A mixture of 45.19 g (0.29 mol) of benzamidine hydrochloride hydrate, 127.42 g (0.59 mol) of 25% sodium methoxide in methanol, 55 mL (0.29 mol) of diethyl ethylmalonate and 175 mL of methanol was heated at reflux for 25 h. The mixture was rotovapped to remove the bulk of the methanol. The residue was diluted with 300 mL of water and the pH was adjusted to 7 with concentrated hydrochloric acid. The solid precipitate was collected by filtration and dried under vacuum at 50° C. to afford 31.89 g (51%) of crude 5-ethyl-6-hydroxy-2-phenyl-4(3H)-pyrimidinone as a pale yellow solid. 1H-NMR (d6-DMSO) δ 1.05(3H,t), 2.39(2H,q), 7.5(3H,m), 8.1(2H,m).

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