Reacción #1095866

ord-e8bc12bbbf184449afb3ff170682ebb5

Ecuación de reacción

C1CCNC1
pyrrolidine
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(N2CCCC2)ncn1
4-(2-butynyloxy)-6-(1-pyrrolidinyl)pyrimidine
Rendimiento 78.4%

Disolventes

Condiciones de reacción

Temperatura
57.5°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 71 mg of pyrrolidine was added therein, and the mixture was stirred for 4 hours at 55-60° 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 170 mg of 4-(2-butynyloxy)-6-(1-pyrrolidinyl)pyrimidine (hereinafter, referred to as Compound (17)).

Fuente

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