تفاعل #77513

معادلة التفاعل

trans 2-isopropyl-[1,3]dioxan-5-ylamine

1-chloro-4-[(6-hydroxy-pyridin-3-yl)methyl]-isoquinoline

tributylamine

→

trans 1-(2-isopropyl-[1,3]dioxan-5-ylamino)-4-[(6-hydroxy-pyridin-3-yl)methyl]-isoquinoline

المذيبات

EtOAc

NaHCO3

ظروف التفاعل

المعالجة

1. 1
   أخرىthe aqueous layer is separated
2. 2
   استخلاصextracted twice with EtOAc
3. 3
   غسيلThe organic phases are washed with brine
4. 4
   تجفيفdried (Na2SO4)
5. 5
   تركيزconcentrated in vaccuo

الإجراء التجريبي

In a sealed glass bottle under N2-atmosphere, 424 mg (2.92 mmol) of trans 2-isopropyl-[1,3]dioxan-5-ylamine, 396 mg (1.46 mmol) of 1-chloro-4-[(6-hydroxy-pyridin-3-yl)methyl]-isoquinoline (contains 1-iodo derivative) and 2 ml of tributylamine are stirred at 150° C. for 48 h. The resulting mixture is diluted with EtOAc and NaHCO3-solution, the aqueous layer is separated and extracted twice with EtOAc. The organic phases are washed with brine, dried (Na2SO4) and concentrated in vaccuo. “Reversed Phase” medium-pressure chromatography (water/acetonitrile/TFA) yields trans 1-(2-isopropyl-[1,3]dioxan-5-ylamino)-4-[(6-hydroxy-pyridin-3-yl)methyl]-isoquinoline; FAB-MS; (M+H)+=286; HPLC(gradient20-100) tRet=8.6.

المصدر