Reaktion #316510

Reaktionsgleichung

methanol

2-methyl-5-nitropyrimidine-4,6-diol

benzaldehyde

piperidine

→

5-nitro-2-[(E)-2-phenylvinyl]pyrimidine-4,6-diol

Ausbeute 63.1%

Lösungsmittel

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe temperature was then increased to 120° C. for 30 min
2. 2
   workup.ADDITIONwere added sequentially
3. 3
   FiltrationThe resulting solid was collected by filtration
4. 4
   Waschenwashed with 5% aqueous hydrochloric acid

Vorschrift

A mixture of 2-methyl-5-nitropyrimidine-4,6-diol (4.7 g, 27.5 mmol) and benzaldehyde (42 mL, 414 mmol) was treated with piperidine (21.3 mL, 215.3 mmol). The reaction mixture was heated to 90° C. for 2 hrs. The temperature was then increased to 120° C. for 30 min. After cooling the reaction mixture to ambient, methanol (10 mL) and diethyl ether (200 mL) were added sequentially. The resulting solid was collected by filtration and washed with 5% aqueous hydrochloric acid to give 5-nitro-2-[(E)-2-phenylvinyl]pyrimidine-4,6-diol (4.5 g). 1H NMR (400 MHz, DMSO-d6): δ 8.15 (d, 1H, J=16.4 Hz), 7.15 (m, 2H), 7.54 (m, 3H), 6.81 (d, 1H, J=16.4 Hz). MS (m/z) 260 (M+1).

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