Reacción #84666

Ecuación de reacción

2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline

methyl (3R,4R)-3-amino-4-hydroxycyclopentane-1-carboxylate

DBU

→

(1S,3R,4R)-methyl 3-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)-4-hydroxycyclopentanecarboxylate

Rendimiento 67.8%

Disolventes

acetonitrile

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was purged with N2 for 5 minutes
2. 2
   TemperaturaAfter cooling to room temperature
3. 3
   Otrothe solvent was removed under reduced pressure

Procedimiento

2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline (0.576 g, 1.558 mmol), methyl (3R,4R)-3-amino-4-hydroxycyclopentane-1-carboxylate (0.372 g, 2.337 mmol) were taken up in acetonitrile (3 ml) and DBU (0.470 ml, 3.12 mmol) was added. The reaction was purged with N2 for 5 minutes then heated to 65° C. overnight. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was purified via flash chromatography (0-100% Hex/EtOAc; 12 g column), and (1S,3R,4R)-methyl 3-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)-4-hydroxycyclopentanecarboxylate (0.520 g, 1.056 mmol, 67.8% yield) was recovered. MS (ES+) C23H23Cl2N3O5 requires: 492, found: 493 [M+H]+.

Fuente