Reaktion #1095869

ord-04f37ee08a704638b9cb3bf1fe497305

Reaktionsgleichung

CC1CCCCN1
2-methylpiperidine
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(N2CCCCC2C)ncn1
4-(2-butynyloxy)-6-(2-methylpiperidino)pyrimidine
Ausbeute 27.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
120°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONwas added
  2. 2
    TemperaturThe reaction mixture was cooled to near room temperature
  3. 3
    Waschenthe mixture was washed with a saturated sodium chloride aqueous solution three times
  4. 4
    TrocknenThe organic layers were dried over anhydrous magnesium sulfate
  5. 5
    Einengenconcentrated

Vorschrift

Into 2 ml of N,N-dimethylformamide was resolved 183 mg of 4-chloro-6-(2-butynyloxy)pyrimidine, 166 mg of potassium carbonate and 99 mg of 2-methylpiperidine was added therein, and the mixture was stirred for 4 hours at 80° C. and 3 hours at 120° 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 66 mg of 4-(2-butynyloxy)-6-(2-methylpiperidino)pyrimidine (hereinafter, referred to as Compound (20)).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07973028B2uspto-grants-2011_07