Reaktion #316509

Reaktionsgleichung

nitric acid

4,6-dihydroxy-2-methylpyrimidine

→

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

Lösungsmittel

—

ice water

trifluoroacetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise over a period of 30 minutes
2. 2
   workup.ADDITIONDuring addition the internal temperature
3. 3
   Temperaturwas maintained below 15° C
4. 4
   workup.ADDITIONAfter the addition
5. 5
   Sonstigethe cooling was removed
6. 6
   workup.ADDITIONWater (50 mL) was added to the reaction mixture
7. 7
   Filtrationthe resulting solid was filtered
8. 8
   Sonstigedried under vacuum

Vorschrift

Powdered 4,6-dihydroxy-2-methylpyrimidine (9 g, 71 mmol) was dissolved in trifluoroacetic acid (54 mL). The reaction mixture was cooled in ice-water as nitric acid (4.3 mL) was added dropwise over a period of 30 minutes. During addition the internal temperature was maintained below 15° C. After the addition, the cooling was removed and the reaction stirred overnight. Water (50 mL) was added to the reaction mixture and the resulting solid was filtered and dried under vacuum to obtain 2-methyl-5-nitropyrimidine-4,6-diol (5.8 g). 1H NMR (400 MHz, DMSO-d6): δ 12.97 (br, 2H), 2.32 (s, 3H). MS (m/z) 172 (M+1).

Quelle