Reacción #1095865

ord-f3b780e9ae414faa8dc4726136e57c52

Ecuación de reacción

C1CCNCC1
piperidine
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(N2CCCCC2)ncn1
4-(2-butynyloxy)-6-piperidinopyrimidine
Rendimiento 77.1%

Disolventes

Condiciones de reacción

Temperatura
80°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 85 mg of piperidine was added therein, and the mixture was stirred for 5 hours at 80° 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 178 mg of 4-(2-butynyloxy)-6-piperidinopyrimidine (hereinafter, referred to as Compound (16)).

Fuente

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