反応 #3542

反応方程式

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

formic acid

→

title compound

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

溶媒

water

反応条件

後処理

1. 1
   ろ過The reaction was filtered
2. 2
   濃縮the filtrate was concentrated in vacuo
3. 3
   抽出extracted with ethyl acetate three times
4. 4
   ろ過The aqueous layer was filtered through a fiberglass
5. 5
   ろ過filter
6. 6
   workup.ADDITIONto disperse the emulsion that
7. 7
   洗浄The aqueous filtrate was washed with ethyl acetate
8. 8
   ろ過filtered
9. 9
   洗浄washed with saturated sodium chloride
10. 10
    乾燥dried with magnesium sulfate
11. 11
    濃縮concentrated in vacuo
12. 12
    洗浄Chromatography down silica gel, eluting with ethyl acetate:hexane (2:1)

実験手順

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+.

出典