Reaktion #3263

Reaktionsgleichung

5-cyano-4-methylamino-2-methylsulfanyl-pyrimidine

water

→

4-Methylamino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde

Lösungsmittel

formic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe solids were filtered
2. 2
   Waschenwashed with 40 mL of 50% aqueous formic acid
3. 3
   TemperaturWith ice bath cooling
4. 4
   workup.ADDITIONa cold saturated solution of potassium carbonate was added slowly to the green filtrate until complete precipitation of a solid
5. 5
   ExtraktionThe solid was extracted into 200 mL of ethyl acetate
6. 6
   Trocknenthe solution was dried (potassium carbonate)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated

Vorschrift

A solution of 4.00 g (0.022 mol) of 5-cyano-4-methylamino-2-methylsulfanyl-pyrimidine (from Example 3) in 150 mL of 50% aqueous formic acid was reacted with 6.0 g of water-wet Raney Nickel. The mixture was stirred at 25° C. for 12 hours. The solids were filtered and washed with 40 mL of 50% aqueous formic acid. With ice bath cooling, a cold saturated solution of potassium carbonate was added slowly to the green filtrate until complete precipitation of a solid was achieved (pH is still acidic; pH about 5). The solid was extracted into 200 mL of ethyl acetate, and the solution was dried (potassium carbonate), filtered, and concentrated; wt 2.30 g (57%); mp 98°-100° C.; tlc (1:1 hexane:ethyl acetate) one spot Rf 0.5.

Quelle