Reaktion #72425

Reaktionsgleichung

MeOH CHCl3

H2O

4-methylpyrimidine

→

Pyrimidine-4-carboxylic Acid

Lösungsmittel

DCM

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   Sonstigeto remove selenium waste
3. 3
   EinengenThe filtrate was concentrated
4. 4
   Sonstigeto give a residue that
5. 5
   Filtrationthe precipitated solid was filtered
6. 6
   Waschenwashed with acetone (2×20 mL)
7. 7
   Sonstigedried
8. 8
   Sonstigeto provide (BB12) (3.1 g, 58%) as a brown solid

Vorschrift

To a solution of 4-methylpyrimidine (4 g, 46.5 mmol) in pyridine (20 mL) was added SeO2 (8.7 g, 79.06 mmol) at room temperature. The reaction mixture was then heated to 60° C. for 2 h, and then stirred at room temperature for 16 h. The reaction mixture was diluted with DCM (50 mL) and filtered to remove selenium waste. The filtrate was concentrated to give a residue that was stirred with H2O (20 mL), the precipitated solid was filtered and washed with acetone (2×20 mL) and dried to provide (BB12) (3.1 g, 58%) as a brown solid. Rf: 0.2 (40% MeOH/CHCl3). 1H NMR (400 MHz, DMSO-d6): δ 13.8 (1H, br s), 9.37 (1H, s), 9.07 (1H, d, J=5.2 Hz), 8.01 (1H, d, J=4 Hz); m/z 123 (M−H)−.

Quelle