Reacción #1702135

ord-b81676a021b64a0180c90c92c48b8a66

Ecuación de reacción

COc1cccc(CCCNc2nc(Cl)ncc2Cl)c1
2,5-dichloro-N-[3-(3-methoxyphenyl)propyl]pyrimidin-4-amine
Nc1cccc(CO)c1
3-aminobenzyl alcohol
Cc1ccc(S(=O)(=O)O)cc1.O
p-toluenesulfonic acid monohydrate
COc1cccc(CCCNc2nc(Nc3cccc(CO)c3)ncc2Cl)c1
desired product
Rendimiento 80.9%
COc1cccc(CCCNc2nc(Nc3cccc(CO)c3)ncc2Cl)c1
{3-[(5-Chloro-4-{[3-(3-methoxyphenyl)propyl]amino}pyrimidin-2-yl)amino]phenyl}methanol
Rendimiento 80.9%

Disolventes

Condiciones de reacción

Temperatura
100°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaAfter cooling
  2. 2
    Filtraciónthe mixture was filtered under vacuum
  3. 3
    LavadoThe cake was washed with cold EtOAc

Procedimiento

To a solution of 2,5-dichloro-N-[3-(3-methoxyphenyl)propyl]pyrimidin-4-amine (0.70 g, 2.2 mmol) and 3-aminobenzyl alcohol (0.38 g, 3.0 mmol) in 1,4-dioxane (19.1 mL) was added p-toluenesulfonic acid monohydrate (0.16 g, 0.82 mmol). The mixture was heated at 100° C. for 16 hours and the reaction was complete. After cooling, the mixture was filtered under vacuum. The cake was washed with cold EtOAc and then H2O to give the desired product as an off-white powder (0.71 g, 79%). LCMS for C21H24ClN4O2 (M+H)+: m/z=399.1.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08765727B2uspto-grants-2014_07