Reaktion #69079

Reaktionsgleichung

dichloromethane

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

lithium hydroxide monohydrate

3-(6-chloroquinolin-4-yloxy)propyl bromide

→

diaminopyrimidine

Ausbeute 55.0%

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

Ausbeute 55.0%

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe reaction mixture was left
2. 2
   workup.STIRRINGstirring at 25° C. overnight
3. 3
   SonstigeDMF was partially removed under reduced pressure
4. 4
   Sonstigeto give residue
5. 5
   Filtrationfiltered
6. 6
   Sonstigeto give white solid
7. 7
   SonstigeRecrystallization with aqueous methanol and hot water

Vorschrift

2,4-Diamino-6-ethyl-5-hydroxypyrimidine (1.39 g, 9 mmol) was added to a stirred solution of lithium hydroxide monohydrate (1.32 g, 31.50 mmol) in DMF (5 mL) and the reaction mixture was stirred at 25° C. for 1 hour. A solution of 3-(6-chloroquinolin-4-yloxy)propyl bromide (2.71 g, 9 mmol) in DMF (3 mL) was added and the reaction mixture was left stirring at 25° C. overnight. DMF was partially removed under reduced pressure to give residue. The residue was digested with dichloromethane and filtered to give white solid. Recrystallization with aqueous methanol and hot water afforded the desired diaminopyrimidine as white solid (1.85 g, 55%, m.p. 230-231° C. (dec.)). 1H NMR (500 MHz, DMSO-d6): 0.91 (3H, t, J=7.6 Hz), 2.26 (2H, q, J=7.6 Hz), 2.31 (2H, m), 3.86 (2H, t, J=6 Hz), 4.45 (2H, t, J=5.9 Hz), 5.59 (2H, s), 6.17, (2H, s), 7.15 (1H, d, J=5.3 Hz), 7.76 (1H, dd, J=9.0, 2.4 Hz), 7.98 (1H, d, J=9.0 Hz), 8.14 (1H, d, J=2.4 Hz), 8.77 (1H, d, J=5.2 Hz).

Quelle