Reacción #1095876

ord-dc1f4bd44c56404e93f25b633caeec5a

Ecuación de reacción

CC1(C)CCNC1
3,3-dimethylpyrrolidine
CN(C)C=O
N,N-dimethylformamide
CC#CCOc1cc(Cl)ncn1
4-(2-butynyloxy)-6-chloropyrimidine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC#CCOc1cc(N2CCC(C)(C)C2)ncn1
4-(2-butynyloxy)-6-(3,3-dimethylpyrrolidin-1-yl)pyrimidine
Rendimiento 22.2%

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 4 ml of N,N-dimethylformamide was resolved 0.37 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.56 g of potassium carbonate and 0.2 g of 3,3-dimethylpyrrolidine was added therein, and the mixture was stirred for 6 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 0.11 g of 4-(2-butynyloxy)-6-(3,3-dimethylpyrrolidin-1-yl)pyrimidine (hereinafter, referred to as Compound (27)).

Fuente

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