反应详情

Concentrated hydrochloric acid (5 mL) was slowly added to a solution of N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]acetamide (15.94 g, 57.9 mmol) in absolute ethanol (100 mL). A precipitate formed immediately and the mixture thickened. Ethanol (50 mL) was added followed by the addition of concentrated hydrochloric acid (119.5 mL). The reaction mixture was heated at reflux for 2 days. The solvents were removed under reduced pressure. Water (250 mL) was added to the residue, solid potassium carbonate was added until the pH reached 7 at which time chloroform (250 mL) was added. Sodium carbonate addition was resumed until the pH reached 10, then 50% sodium hydroxide was added until the pH reached 14. The mixture was diluted with additional chloroform (500 mL) and then stirred at ambient temperature for 2 days. The organic layer was separated, dried with magnesium sulfate and then concentrated under reduced pressure. The residue was recrystallized from acetonitrile to provide 8.42 g of 1-(3-aminopropyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine as an off-white crystalline solid, m.p. 191.5-191.9° C. Analysis: Calculated for C12H19N5·0.25 H2O: % C, 60.61; % H, 8.26; % N, 29.45; Found: % C, 60.50; % H, 8.28; % N, 29.57.

1. customA precipitate formed immediately
2. temperatureThe reaction mixture was heated
3. temperatureat reflux for 2 days
4. customThe solvents were removed under reduced pressure
5. additionWater (250 mL) was added to the residue, solid potassium carbonate
6. additionwas added until the pH
7. additionwas added
8. additionSodium carbonate addition
9. addition50% sodium hydroxide was added until the pH
10. additionThe mixture was diluted with additional chloroform (500 mL)
11. customThe organic layer was separated
12. dry with materialdried with magnesium sulfate
13. concentrationconcentrated under reduced pressure
14. customThe residue was recrystallized from acetonitrile