Реакция #3542

Уравнение реакции

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

formic acid

→

title compound

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

Растворители

water

Условия реакции

Обработка

1. 1
   ФильтрацияThe reaction was filtered
2. 2
   Концентрированиеthe filtrate was concentrated in vacuo
3. 3
   Экстракцияextracted with ethyl acetate three times
4. 4
   ФильтрацияThe aqueous layer was filtered through a fiberglass
5. 5
   Фильтрацияfilter
6. 6
   workup.ADDITIONto disperse the emulsion that
7. 7
   ПромывкаThe aqueous filtrate was washed with ethyl acetate
8. 8
   Фильтрацияfiltered
9. 9
   Промывкаwashed with saturated sodium chloride
10. 10
    Сушкаdried with magnesium sulfate
11. 11
    Концентрированиеconcentrated in vacuo
12. 12
    ПромывкаChromatography down silica gel, eluting with ethyl acetate:hexane (2:1)

Методика

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+.

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