Reacción #42824

ord-10f01cf55aa34dfcb2edcde7934779c7

Ecuación de reacción

[Cl-].[NH4+]
ammonium chloride
CC#CCOc1cc(Cl)ncn1
4-(2-butynyloxy)-6-chloropyrimidine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC1(C)CNCC(C)(C)C1.Cl
3,3,5,5-tetramethylpiperidine hydrochloride
CC#CCOc1cc(N2CC(C)(C)CC(C)(C)C2)ncn1
4-(2-butynyloxy)-6-(3,3,5,5-tetramethylpiperidino)pyrimidine
Rendimiento 73.1%

Disolventes

Condiciones de reacción

Temperatura
60°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 2 ml of acetonitrile were added 0.20 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.45 g of potassium carbonate and 0.24 g of 3,3,5,5-tetramethylpiperidine hydrochloride, and the mixture was stirred for 4 hours at 60° 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 0.23 g of 4-(2-butynyloxy)-6-(3,3,5,5-tetramethylpiperidino)pyrimidine (hereinafter, referred to as Compound (38)).

Fuente

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