反応 #3258

反応方程式

2-azido-5-cyano-4-methylaminopyrimidine

2-azido-5-cyano-4-methylamino-pyrimidine

formic acid

hydrogen

→

2-amino-4-methylamino-5-pyrimidinecarboxaldehyde

反応条件

後処理

1. 1
   workup.STIRRINGwas shaken at room temperature
2. 2
   workup.STIRRINGthe mixture shaken overnight
3. 3
   その他The catalyst was removed by filtration
4. 4
   その他the filtrate was evaporated under high vacuum
5. 5
   ろ過filtered
6. 6
   その他The insoluble material was collected
7. 7
   workup.DISSOLUTIONdissolved in 450 mL of boiling water
8. 8
   ろ過The aqueous solution was filtered
9. 9
   ろ過The precipitated product was collected by filtration
10. 10
    その他recrystallized from ethanol

実験手順

To a suspension of 2-azido-5-cyano-4-methylaminopyrimidine (22.24 g) from Example 5 in 400 mL of 50% aqueous formic acid was added Raney Nickel catalyst (5 g). The reaction mixture was shaken under an atmosphere of hydrogen (40.1 psi) in a Parr hydrogenation apparatus. There was a vigorous evolution of gas as the mixture was shaken at room temperature. After 30 minutes the apparatus was vented, additional Raney Nickel (5 g) was added, the apparatus recharged with hydrogen, and the mixture shaken overnight. The catalyst was removed by filtration and the filtrate was evaporated under high vacuum. The residue was suspended in water and filtered. The insoluble material was collected and dissolved in 450 mL of boiling water. The aqueous solution was filtered and the pH of the filtrate was adjusted to 7 with 1N sodium hydroxide. The precipitated product was collected by filtration and recrystallized from ethanol to give 5.0 g of 2-amino-4-methylamino-5-pyrimidinecarboxaldehyde.

出典