Reaktion #580988

Reaktionsgleichung

NH3

trans-[4-(8-chloro-1-iodoimidazo[1,5-a]pyrazin-3-yl)cyclohexyl]methanol

THF

→

desired product

trans-[4-(8-Amino-1-iodoimidazo[1,5-a]pyrazin-3-yl)cyclohexyl]methanol

Lösungsmittel

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAmmonia gas was bubbled vigorously into the solution for 8 min
2. 2
   Sonstigethen the bomb was tightly sealed
3. 3
   Temperaturheated to 120° C. for 20 h
4. 4
   SonstigeThe crude reaction mixture
5. 5
   Einengenwas concentrated in vacuo
6. 6
   SonstigeThe mixture was purified by a silica gel glass column chromatography [eluted with 1:1 CH2Cl2/EtOAc to 10% ˜7 N NH3 in MeOH/CHCl3]

Vorschrift

trans-[4-(8-chloro-1-iodoimidazo[1,5-a]pyrazin-3-yl)cyclohexyl]methanol (26.50 g, 67.66 mmol) was charged in a 400 mL steel bomb and was dissolved in 2M NH3 in isopropanol (300 mL) and anhydrous THF (10 mL). The reaction mixture was cooled to −78° C. Ammonia gas was bubbled vigorously into the solution for 8 min; then the bomb was tightly sealed and heated to 120° C. for 20 h. The crude reaction mixture was concentrated in vacuo, then the reaction residue was taken up with MeOH/CHCl3, loaded onto silica gel. The mixture was purified by a silica gel glass column chromatography [eluted with 1:1 CH2Cl2/EtOAc to 10% ˜7 N NH3 in MeOH/CHCl3] to afford the desired product as a beige cream white solid; MS (ES+): m/z 373.01 (100) [MH+], 373.98 (50) [MH+2]; tR(polar-5 min/openlynx) 1.57 min.

Quelle