Réaction #1095867

ord-8f9a4f802ec54921ba08b4c83ea0807e

Équation de réaction

CC1CCNCC1
4-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(N2CCC(C)CC2)ncn1
4-(2-butynyloxy)-6-(4-methylpiperidino) pyrimidine
Rendement 84.1%

Conditions de réaction

Température
80°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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 4-methylpiperidine was added therein, and the mixture was stirred for 4 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 206 mg of 4-(2-butynyloxy)-6-(4-methylpiperidino) pyrimidine (hereinafter, referred to as Compound (18)).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07973028B2uspto-grants-2011_07