Reacción #42823

ord-2ad59e5f749d454e82d839a242595785

Ecuación de reacción

[Cl-].[NH4+]
ammonium chloride
CC#CCOc1cc(Cl)ncn1
4-(2-butynyloxy)-6-chloropyrimidine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC1CNCC1C.Cl
3,4-dimethylpyrrolidine hydrochloride
CC#CCOc1cc(N2CC(C)C(C)C2)ncn1
4-(2-butynyloxy)-6-(3,4-dimethylpyrrolidin-1-yl) pyrimidine
Rendimiento 104.2%

Disolventes

Condiciones de reacción

Temperatura
70°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe reaction mixture was cooled to near room temperature
  2. 2
    Extracciónthe mixture was extracted with tert-butyl methyl ether three times
  3. 3
    LavadoThe organic layers were washed with a saturated sodium chloride aqueous solution
  4. 4
    Secadodried over anhydrous magnesium sulfate
  5. 5
    Concentraciónconcentrated

Procedimiento

Into 3 ml of acetonitrile were added 0.30 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.68 g of potassium carbonate and 0.33 g of 3,4-dimethylpyrrolidine hydrochloride (cis and trans diastereomer mixture), and the mixture was stirred for 4 hours at 70° C. The reaction mixture was cooled to near room temperature, a saturated ammonium chloride aqueous solution was added therein, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.42 g of 4-(2-butynyloxy)-6-(3,4-dimethylpyrrolidin-1-yl) pyrimidine (hereinafter, referred to as Compound (37)).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07732448B2uspto-grants-2010_06