Potassium Carbonate → 4-(2,6-Difluorobenzyloxy)-6-(2-butynyloxy)pyrimidine

HRID 1592136

Reaktionsgleichung

Reaktionsgleichung von HRID 1592136
[CH2:1]([O:5][C:6]1[CH:11]=[C:10](S(C)(=O)=O)[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[F:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:24]=1[CH2:25][OH:26].[Cl-].[NH4+]>CN(C)C=O>[F:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:24]=1[CH2:25][O:26][C:10]1[CH:11]=[C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])[N:7]=[CH:8][N:9]=1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 879212,6-Difluorobenzyl alcoholHCID 22599863HCID 22599863, Verbindung

Produkt 1

HCID 225997444-(2,6-Difluorobenzyloxy)-6-(2-butynyloxy)pyrimidineAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To 2 ml of N,N-dimethylformamide were added 0.15 g of 4-(2-butynyloxy)-6-methanesulfonylpyrimidine, 0.14 g of potassium carbonate, and 0.16 g of 2,6-difluorobenzylalcohol, followed by stirring at 50° C. for 7 hours. The reaction mixture was then left for cooling to room temperature and poured into a saturated aqueous ammonium chloride solution, which was extracted three times with chloroform. The chloroform layers were combined, washed with diluted hydrochloric acid and then with water, and dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 0.14 g of 4-(2,6-difluorobenzyloxy)-6-(2-butynyloxy)pyrimidine (the present compound (68)).

Aufarbeitung

  1. waitThe reaction mixture was then left
  2. temperaturefor cooling to room temperature
  3. extractionwas extracted three times with chloroform
  4. washwashed with diluted hydrochloric acid
  5. dry with materialwith water, and dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7eaf3970bf9f4a24809130dda075deff
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07291730B2

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