2-Butyn-1-ol → 4-(2-Butynyloxy)-6-chloro-5-methylpyrimidine

HRID 14564

Reaktionsgleichung

Reaktionsgleichung von HRID 14564
[H-].[Na+].[CH2:3]([OH:7])[C:4]#[C:5][CH3:6].[Cl:8][C:9]1[C:14]([CH3:15])=[C:13](Cl)[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:8][C:9]1[C:14]([CH3:15])=[C:13]([O:7][CH2:3][C:4]#[C:5][CH3:6])[N:12]=[CH:11][N:10]=1

Komponenten

6

Edukt 4

HCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 8188604,6-Dichloro-5-methylpyrimidine

Produkt 1

HCID 225997914-(2-Butynyloxy)-6-chloro-5-methylpyrimidineAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

0.32 g of sodium hydride (60% oil suspension) was suspended in 12 ml of tetrahydrofuran. 2 ml of tetrahydrofuran solution of 0.43 g of 2-butyn-1-ol was added dropwise at room temperature therein slowly, and the mixture was stirred for 20 minutes. Into the mixture was added dropwise 2 ml of tetrahydrofuran solution of 1 g of 4,6-dichloro-5-methylpyrimidine at 0° C. slowly, and stirred for 2 hours. The reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 1.1 g of 4-chloro-6-(2-butynyloxy)-5-methylpyrimidine.

Aufarbeitung

  1. stirringstirred for 2 hours
  2. extractionthe mixture was extracted with tert-butyl methyl ether three times
  3. washThe organic layers were washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-527f50ac5328407d99b6df972cffea6b
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732448B2

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