Reaction #3542

Reaction equation

4-Amino-2-phenylamino-pyrimidine-5-carbonitrile

formic acid

→

title compound

4-Amino-2-phenylamino-pyrimidine-5-carboxaldehyde

Solvents

water

Conditions

Workup

1. 1
   FiltrationThe reaction was filtered
2. 2
   Concentrationthe filtrate was concentrated in vacuo
3. 3
   Extractionextracted with ethyl acetate three times
4. 4
   FiltrationThe aqueous layer was filtered through a fiberglass
5. 5
   Filtrationfilter
6. 6
   workup.ADDITIONto disperse the emulsion that
7. 7
   WashThe aqueous filtrate was washed with ethyl acetate
8. 8
   Filtrationfiltered
9. 9
   Washwashed with saturated sodium chloride
10. 10
    Dryingdried with magnesium sulfate
11. 11
    Concentrationconcentrated in vacuo
12. 12
    WashChromatography down silica gel, eluting with ethyl acetate:hexane (2:1)

Procedure

4-Amino-2-phenylamino-pyrimidine-5-carbonitrile (2.00 g) obtained from Example 71 was combined with wet Raney nickel (2.00 g), 98% formic acid (60 mL) and water (40 mL) in a Parr shaker. The reaction was placed under hydrogen (42 psi) and shaken for 20 minutes. The reaction was filtered, and the filtrate was concentrated in vacuo. The residue was suspended in water, made basic with saturated sodium bicarbonate, and extracted with ethyl acetate three times. The aqueous layer was filtered through a fiberglass filter to disperse the emulsion that was present. The aqueous filtrate was washed with ethyl acetate. The ethyl acetate washes were combined, filtered, washed with saturated sodium chloride, dried with magnesium sulfate and concentrated in vacuo. Chromatography down silica gel, eluting with ethyl acetate:hexane (2:1) gave 0.73 g of the title compound, CIMS (1% NH3 in CH4): 243=M+ +C2H5, 215=M+ +H (Base), 214=M+.

Source