Reaktion #69089

Reaktionsgleichung

1-(3-bromopropyl)indole

2,4-diamino-6-ethyl-5-hydroxypyrimidine

lithium hydroxide monohydrate

→

solid

Ausbeute 48.0%

2,4-diamino-6-ethyl-5-(3-(1-indolyl)propoxy)pyrimidine

Ausbeute 48.0%

Lösungsmittel

DMF

DMF

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe reaction mixture was left
2. 2
   workup.STIRRINGstirring at 25° C. overnight
3. 3
   Extraktionextracted with water
4. 4
   SonstigeThe dichloromethane layer was evaporated
5. 5
   Sonstigethe residue was recrystallized from aqueous methanol

Vorschrift

2,4-diamino-6-ethyl-5-hydroxypyrimidine (0.4625 g, 3 mmol) was added to a stirred solution of lithium hydroxide monohydrate (0.3147 g, 7.5 mmol) in DMF (2 mL) and the reaction mixture was stirred for 1 hour. A solution of 1-(3-bromopropyl)indole (0.7144 g, 3 mmol) in DMF (1 mL) was added and the reaction mixture was left stirring at 25° C. overnight. The reaction was diluted with dichloromethane and extracted with water. The dichloromethane layer was evaporated and the residue was recrystallized from aqueous methanol. The product was obtained as a slightly yellow solid (0.4484 g, 48%). 1H NMR (DMSO-d6): 1.02 (3H, t, J=7.5 Hz), 2.20 (2H, m), 2.32 (2H, q, J=7.5 Hz), 3.60 (2H, t, J=6.3 Hz), 4.34 (2H, t, J=7.2 Hz), 5.56 (2H, s), 6.07 (2H, s), 6.43 (1H, d, J=3.1 Hz), 7.01 (1H, m), 7.13 (1H, m), 7.40 (1H, d, J=3.1 Hz), 7.50 (1H, d, J=8.3 Hz), 7.54 (1H, d, J=7.8 Hz).

Quelle