Réaction #42819

Équation de réaction

ammonium chloride

sodium hydride

3,3-dimethylpiperidine hydrochloride

4-(2-butynyloxy)-6-chloro-5-fluoropyrimidine

→

4-(2-butynyloxy)-6-(3,3-dimethylpiperidino)-5-fluoropyrimidine

Rendement 18.1%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Extractionthe mixture was extracted with tert-butyl methyl ether three times
2. 2
   LavageThe organic layers were washed with a saturated sodium chloride aqueous solution
3. 3
   Séchagedried over anhydrous magnesium sulfate
4. 4
   Concentrationconcentrated

Mode opératoire

0.12 g of sodium hydride (60% oil suspension) was suspended in 2 ml of tetrahydrofuran. 0.18 g of 3,3-dimethylpiperidine hydrochloride and 0.20 g of 4-(2-butynyloxy)-6-chloro-5-fluoropyrimidine were added therein, and the mixture was stirred for 1 hour at 60%. After the reaction mixture was cooled to near room temperature, a saturated ammonium chloride aqueous solution was added therein, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.05 g of 4-(2-butynyloxy)-6-(3,3-dimethylpiperidino)-5-fluoropyrimidine (hereinafter, referred to as Compound (32)).

Source