Reaktion #69093

Reaktionsgleichung

ethyl 4-(2-(3-bromopropoxy)phenoxy)butanoate

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

lithium hydroxide monohydrate

→

diaminopyrimidine

Ausbeute 59.0%

2,4-diamino-6-ethyl-5-(3-(2-(3-carboxypropoxy)phenoxy)propoxy)pyrimidine

Ausbeute 59.0%

Lösungsmittel

DMF

DMF

water

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
   Extraktionextracted with dichloromethane
6. 6
   Sonstigeto give white solid
7. 7
   SonstigeRecrystallization with acetone

Vorschrift

2,4-Diamino-6-ethyl-5-hydroxypyrimidine (0.4625 g, 3 mmol) was added to a stirred solution of lithium hydroxide monohydrate (0.4406 g, 10.5 mmol) in DMF (4 mL) and the reaction mixture was stirred at 25° C. for 1 hour. A solution of ethyl 4-(2-(3-bromopropoxy)phenoxy)butanoate (1.0357 g, 3 mmol) in DMF (1 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 diluted with water and extracted with dichloromethane. The aqueous layer was neutralized with dilute HCl to give white solid. Recrystallization with acetone afforded the desired diaminopyrimidine as white solid (0.6911 g, 59%, m.p. 204-206° C.). 1H NMR (400 MHz, DMSO-d6): 1.10 (3H, t, J=7.5 Hz), 1.91 (2H, m), 2.14 (2H, m), 2.31-2.39 (4H, m), 3.78 (2H, t, J=6.1 Hz), 3.96 (2H, t, J=6.4 Hz), 4.13 (2H, t, J=6.1 Hz), 5.60 (2H, s), 6.09 (2H, s), 6.86-6.90 (2H, m), 6.95-7.01 (2H, m).

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