Réaction #1095865

ord-f3b780e9ae414faa8dc4726136e57c52

Équation de réaction

C1CCNCC1
piperidine
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(N2CCCCC2)ncn1
4-(2-butynyloxy)-6-piperidinopyrimidine
Rendement 77.1%

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 85 mg of piperidine was added therein, and the mixture was stirred for 5 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 178 mg of 4-(2-butynyloxy)-6-piperidinopyrimidine (hereinafter, referred to as Compound (16)).

Source

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