反应 #1095855

反应方程式

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

3,5-dimethylpiperidine

→

4-(2-butynyloxy)-5-fluoro-6-(3,5-dimethylpiperidino)pyrimidine

收率 96.4%

溶剂

ethanol

反应条件

后处理

1. 1
   workup.ADDITIONwas added
2. 2
   温度under reflux condition
3. 3
   浓缩concentrated
4. 4
   workup.ADDITIONInto the residue was added a saturated ammonium chloride aqueous solution
5. 5
   萃取the mixture was extracted with tert-butyl methyl ether three times
6. 6
   洗涤The organic layers were washed with a saturated sodium chloride aqueous solution
7. 7
   干燥dried over anhydrous magnesium sulfate
8. 8
   浓缩concentrated

实验过程

Into 3 ml of ethanol was resolved 0.3 g of 4-(2-butynyloxy)-6-chloro-5-fluoropyrimidine, 0.51 g of 3,5-dimethylpiperidine (cis/trans=about 3/1) was added therein, and the mixture was stirred for 8 hours under reflux condition. The reaction mixture was cooled to near room temperature, and concentrated. Into the residue was added 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 0.40 g of 4-(2-butynyloxy)-5-fluoro-6-(3,5-dimethylpiperidino)pyrimidine (hereinafter, referred to as Compound (4)). Compound (4) had the cis/trans diastereomer originated two methyls on the piperidine ring. The ratio of the cis/trans diastereomer was about 3.3/1.

来源