반응 #3542

반응 방정식

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

formic acid

→

title compound

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

용매

water

반응 조건

후처리

1. 1
   여과The reaction was filtered
2. 2
   농축the filtrate was concentrated in vacuo
3. 3
   추출extracted with ethyl acetate three times
4. 4
   여과The aqueous layer was filtered through a fiberglass
5. 5
   여과filter
6. 6
   workup.ADDITIONto disperse the emulsion that
7. 7
   세척The aqueous filtrate was washed with ethyl acetate
8. 8
   여과filtered
9. 9
   세척washed with saturated sodium chloride
10. 10
    건조dried with magnesium sulfate
11. 11
    농축concentrated in vacuo
12. 12
    세척Chromatography down silica gel, eluting with ethyl acetate:hexane (2:1)

실험 절차

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+.

출처