Reaction #1095881

Reaction equation

ammonium chloride

sodium hydride

3,3-dimethylpiperidine hydrochloride

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

→

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

Yield 18.1%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureAfter the reaction mixture was cooled to near room temperature
2. 2
   Extractionthe mixture was extracted with tert-butyl methyl ether three times
3. 3
   WashThe organic layers were washed with a saturated sodium chloride aqueous solution
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrated

Procedure

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° C. 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