Réaction #1095893

Équation de réaction

ammonium chloride

6-chloro-4-(cis-2,6-dimethylpiperidino)pyrimidine

sodium hydride

2-butyn-1-ol

→

4-(2-butynyloxy)-6-(cis-2,6-dimethylpiperidino)pyrimidine

Rendement 91.6%

Solvants

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred for 6 hours at 60° C
2. 2
   Extractionthe mixture was extracted with tert-butyl methyl ether three times
3. 3
   LavageThe organic layers were washed with a saturated sodium chloride aqueous solution
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrated

Mode opératoire

0.06 g of sodium hydride (60% oil suspension) was suspended in 1.5 ml of tetrahydrofuran. 0.3 ml of tetrahydrofuran solution of 0.08 g of 2-butyn-1-ol was added dropwise at room temperature therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.3 ml of tetrahydrofuran solution of 0.19 g of 6-chloro-4-(cis-2,6-dimethylpiperidino)pyrimidine at room temperature, and stirred for 6 hours at 60° C. After the reaction mixture was cooled to near room temperature, 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 a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.20 g of 4-(2-butynyloxy)-6-(cis-2,6-dimethylpiperidino)pyrimidine (hereinafter, referred to as Compound (48)).

Source