Réaction #1095870

ord-05a15af1c2944caf9098e14e05eaabb9

Équation de réaction

CC1CCCN1
2-methylpyrrolidine
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(N2CCCC2C)ncn1
4-(2-butynyloxy)-6-(2-methyl-pyrrolidin-1-yl)pyrimidine
Rendement 89.7%

Conditions de réaction

Température
60°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 2-methylpyrrolidine was added therein, and the mixture was stirred for 7 hours at 60° 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 207 mg of 4-(2-butynyloxy)-6-(2-methyl-pyrrolidin-1-yl)pyrimidine (hereinafter, referred to as Compound (21)).

Source

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