Réaction #42843

Équation de réaction

ammonium chloride

4,6-dichloro-5-fluoropyrimidine

sodium hydride

2-pentyn-1-ol

→

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

Rendement 102.9%

Solvants

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred for 70 minutes
2. 2
   Extractionthe mixture was extracted with tert-butyl methyl ether three times
3. 3
   LavageThe organic layers were washed with water
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrated

Mode opératoire

0.58 g of sodium hydride (60% oil suspension) 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 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.

Source