Reaktion #69098

Reaktionsgleichung

methyl 3-(2-(3-bromopropoxy)phenyl)propanoate

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

lithium hydroxide monohydrate

→

diaminopyrimidine

Ausbeute 58.0%

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

Ausbeute 58.0%

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
   Extraktionfollowed by extraction with dichloromethane
6. 6
   Sonstigeto give white solid
7. 7
   SonstigeRecrystallization from 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 methyl 3-(2-(3-bromopropoxy)phenyl)propanoate (0.9035 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 followed by extraction with dichloromethane. The aqueous layer was neutralized with dil. HCl to give white solid. Recrystallization from acetone afforded the desired diaminopyrimidine as white solid (0.6271 g, 58%, m.p. 155.5-157.5° C.). 1H NMR (400 MHz, DMSO-d6): 1.04 (3H, t, J=7.6 Hz), 2.19 (2H, m), 2.39 (2H, q, J=7.5 Hz), 2.46 (2H, t, J=7.5 Hz), 2.78 (2H, t, J=7.7 Hz), 3.83 (2H, t, J=6.1 Hz), 4.15 (2H, t, J=5.9 Hz), 6.29 (2H, bs), 6.85 (1H, t, J=7.4 Hz), 6.96 (2H, bs), 6.98 (1H, d, J=8.1 Hz), 7.14-7.19 (2H, m).

Quelle