Water → 4-(Methylamino)-2-(methylthio)pyrimidine-5-carbaldehyde
Reaction equation
[C:1]([C:3]1[C:4]([NH:11][CH3:12])=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1)#N.[OH2:13]>C(O)=O>[CH3:12][NH:11][C:4]1[C:3]([CH:1]=[O:13])=[CH:8][N:7]=[C:6]([S:9][CH3:10])[N:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
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.