Reacción #1095869

ord-04f37ee08a704638b9cb3bf1fe497305

Ecuación de reacción

CC1CCCCN1
2-methylpiperidine
CN(C)C=O
N,N-dimethylformamide
CC#CCOc1cc(Cl)ncn1
4-chloro-6-(2-butynyloxy)pyrimidine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC#CCOc1cc(N2CCCCC2C)ncn1
4-(2-butynyloxy)-6-(2-methylpiperidino)pyrimidine
Rendimiento 27.0%

Disolventes

Condiciones de reacción

Temperatura
120°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONwas added
  2. 2
    TemperaturaThe reaction mixture was cooled to near room temperature
  3. 3
    Lavadothe mixture was washed with a saturated sodium chloride aqueous solution three times
  4. 4
    SecadoThe organic layers were dried over anhydrous magnesium sulfate
  5. 5
    Concentraciónconcentrated

Procedimiento

Into 2 ml of N,N-dimethylformamide was resolved 183 mg of 4-chloro-6-(2-butynyloxy)pyrimidine, 166 mg of potassium carbonate and 99 mg of 2-methylpiperidine was added therein, and the mixture was stirred for 4 hours at 80° C. and 3 hours at 120° C. The reaction mixture was cooled to near room temperature, ethyl acetate was added therein, and the mixture was washed with a saturated sodium chloride aqueous solution three times. The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 66 mg of 4-(2-butynyloxy)-6-(2-methylpiperidino)pyrimidine (hereinafter, referred to as Compound (20)).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07973028B2uspto-grants-2011_07