Dimethylformamide → 4-(2-Butynyloxy)-6-(1-pyrrolidinyl)pyrimidine

HRID 14526

Reaktionsgleichung

Reaktionsgleichung von HRID 14526
CN(C)C=O.Cl[C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]#[C:16][CH3:17])[N:10]=[CH:9][N:8]=1.C(=O)([O-])[O-].[K+].[K+].[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>C(OCC)(=O)C>[CH2:14]([O:13][C:11]1[CH:12]=[C:7]([N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[N:8]=[CH:9][N:10]=1)[C:15]#[C:16][CH3:17]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

Produkt 1

HCID 593411244-(2-Butynyloxy)-6-(1-pyrrolidinyl)pyrimidineAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
57.5 °C

Versuchsvorschrift

Into 2 ml of N,N-dimethylformamide was resolved 183 mg of 4-chloro-6-(2-butynyloxy)pyrimidine, 166 mg of potassium carbonate and 71 mg of pyrrolidine was added therein, and the mixture was stirred for 4 hours at 55-60° 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 170 mg of 4-(2-butynyloxy)-6-(1-pyrrolidinyl)pyrimidine (hereinafter, referred to as Compound (17)).

Aufarbeitung

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to near room temperature
  3. washthe mixture was washed with a saturated sodium chloride aqueous solution three times
  4. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9301375205eb495a8f2ee552776a73a0
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732448B2

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