反応 #1095864

反応方程式

ammonium chloride

4-chloro-6-(3,5-dimethylpiperidino) pyrimidine

sodium hydride

2-pentyn-1-ol

→

4-(3,5-dimethylpiperidino)-6-(2-pentynyloxy)pyrimidine

収率 41.3%

溶媒

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   その他obtained the Reference Production Example 6
2. 2
   workup.STIRRINGstirred for 6 hours at room temperature
3. 3
   抽出the mixture was extracted with tert-butyl methyl ether three times
4. 4
   洗浄The organic layers were washed with a saturated sodium chloride aqueous solution
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   濃縮concentrated

実験手順

0.07 g of sodium hydride (60% oil suspension) was suspended in 2 ml of tetrahydrofuran. 0.5 ml of tetrahydrofuran solution of 0.13 g of 2-pentyn-1-ol was added dropwise at 0° C. therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 0.5 ml of tetrahydrofuran solution of 0.3 g of 4-chloro-6-(3,5-dimethylpiperidino) pyrimidine obtained the Reference Production Example 6, and stirred for 6 hours at room temperature. Into the reaction mixture 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 0.15 g of 4-(3,5-dimethylpiperidino)-6-(2-pentynyloxy)pyrimidine (hereinafter, referred to as Compound (15)). Compound (15) had the cis/trans diastereomer originated two methyls on the pyperidine ring. The ratio of the cis/trans diastereomer was about 8.2/1.

出典