Reaktion #1179884

Reaktionsgleichung

ammonium chloride

4,6-dichloro-5-fluoropyrimidine

sodium hydride

2-pentyn-1-ol

→

4-chloro-5-fluoro-6-(2-pentynyloxy)pyrimidine

Ausbeute 102.9%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 70 minutes
2. 2
   Extraktionthe mixture was extracted with tert-butyl methyl ether three times
3. 3
   WaschenThe organic layers were washed with water
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Einengenconcentrated

Vorschrift

0.58 g of sodium hydride (60% oil suspention) was suspended in 20 ml of tetrahydrofuran. 1 ml of tetrahydrofuran solution of 0.88 g of 2-pentyn-1-ol was added dropwise at 0° C. therein slowly, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 5 ml of tetrahydrofuran solution of 2 g of 4,6-dichloro-5-fluoropyrimidine at 0° C., and stirred for 70 minutes. 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 2.31 g of 4-chloro-5-fluoro-6-(2-pentynyloxy)pyrimidine.

Quelle