Reaktion #69084

Reaktionsgleichung

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

lithium hydroxide monohydrate

3-(2-methylquinolin-4-yloxy)propyl bromide

→

title compound

Ausbeute 47.0%

2,4-diamino-6-ethyl-5-(3-(2-methylquinolin-4-yloxy)propoxy)pyrimidine

Ausbeute 47.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   workup.WAITthe reaction mixture was left
3. 3
   SonstigeTwo thirds of the DMF was evaporated under vacuum
4. 4
   workup.ADDITIONthe reaction mixture was poured in water
5. 5
   Sonstigesolid was separated by filtration
6. 6
   Sonstigedried in oven at 80° C
7. 7
   SonstigeThe crude product was purified by column chromatography on silica gel (4% MeOH: 96% CH2Cl2 as eluent)

Vorschrift

A mixture of 2,4-diamino-6-ethyl-5-hydroxypyrimidine (0.539 g, 3.5 mmol) and lithium hydroxide monohydrate (0.294 g, 7.0 mmol) in DMF (10 mL) was stirred at 25° C. for 1 hour after that 3-(2-methylquinolin-4-yloxy)propyl bromide (0.980 g, 3.5 mmol) was added to the reaction mixture and the reaction mixture was left to stir at 25° C. overnight. Two thirds of the DMF was evaporated under vacuum and the reaction mixture was poured in water, solid was separated by filtration and dried in oven at 80° C. The crude product was purified by column chromatography on silica gel (4% MeOH: 96% CH2Cl2 as eluent) to obtain title compound as light yellow solid (0.5814 g, 47%). 1H NMR (400 MHz, DMSO-d6): 0.90 (3H, t, J=7.6 Hz), 2.30 (4H, m), 2.60 (3H, s), 3.86 (2H, t, J=5.9 Hz), 4.41 (2H, t, J=5.9 Hz), 5.59 (2H, s), 6.16 (2H, s), 6.97 (1H, s), 7.46 (1H, t, J=7.7 Hz), 7.67 (1H, t, J=7.7 Hz), 7.84 (1H, d, J=8.4 Hz), 8.09 (1H, d, J=8.2 Hz).

Quelle