Water → 4-(2-Butynyloxy)-6-phenylpyrimidine

HRID 1592106

Reaktionsgleichung

Reaktionsgleichung von HRID 1592106
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[CH2:14]([OH:18])[C:15]#[C:16][CH3:17].[H-].[Na+].O>O1CCCC1>[CH2:14]([O:18][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1)[C:15]#[C:16][CH3:17]

Komponenten

6

Edukt 4

HCID 962WaterHCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 5934294-Chloro-6-phenylpyrimidine

Produkt 1

HCID 225997924-(2-Butynyloxy)-6-phenylpyrimidineAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In 5 ml of tetrahydrofuran were dissolved 186 mg of 4-chloro-6-phenylpyrimidine and 82 mg of 2-butyn-1-ol, to which 47 mg of sodium hydride (60% in oil) was added with stirring at room temperature, followed by further stirring for 3 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The resulting residue was subjected to silica gel column chromatography to give 190 mg of 4-(2-butynyloxy)-6-phenylpyrimidine (the present compound (38)), m.p.: 59.6° C.

Aufarbeitung

  1. stirringby further stirring for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7daf772ff8cf4bb28127b6ce27419e36
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07291730B2

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