Reacción #69098

Ecuación de reacción

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

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

lithium hydroxide monohydrate

→

diaminopyrimidine

Rendimiento 58.0%

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

Rendimiento 58.0%

Disolventes

DMF

DMF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITthe reaction mixture was left
2. 2
   workup.STIRRINGstirring at 25° C. overnight
3. 3
   OtroDMF was partially removed under reduced pressure
4. 4
   Otroto give residue
5. 5
   Extracciónfollowed by extraction with dichloromethane
6. 6
   Otroto give white solid
7. 7
   OtroRecrystallization from acetone

Procedimiento

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).

Fuente