反応 #168118

反応方程式

NaH

4-(4-Isopropyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-yl)phenol

HCl

Chloro-N,N-dimethylacetamide

→

title compound

収率 41.0%

2-[4-(4-Isopropyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-yl)phenoxy]-N,N-dimethylacetamide, dihydrochloride

収率 41.0%

溶媒

DMF

diethyl ether

反応条件

後処理

1. 1
   温度the reaction mixture was heated for 2.5 h at 130° C. in a microwave oven
2. 2
   その他The reaction mixture was evaporated in vacuo
3. 3
   workup.DISSOLUTIONthe residue was redissolved in a mixture of DCM and water
4. 4
   その他The phases were separated
5. 5
   抽出the aqueous phase was extracted with DCM (2×25 mL)
6. 6
   その他The combined organic extracts were evaporated
7. 7
   workup.DISSOLUTIONredissolved in MeOH
8. 8
   その他purified by preparative HPLC Method B
9. 9
   その他This afforded an oil which
10. 10
    その他to give a solid material
11. 11
    その他Recrystallization from acetone and MeOH

実験手順

4-(4-Isopropyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-yl)phenol (0.15 g, 0.404 mmol) was dissolved in DMF (4 mL) in a 5 mL microwave vial. NaH (0.039 g, 1.62 mmol) was added slowly and the mixture was stirred at rt for 30 min. Chloro-N,N-dimethylacetamide (0.147 g, 1.21 mmol) was added and the reaction mixture was heated for 2.5 h at 130° C. in a microwave oven. The reaction mixture was evaporated in vacuo and the residue was redissolved in a mixture of DCM and water. The phases were separated and the aqueous phase was extracted with DCM (2×25 mL). The combined organic extracts were evaporated, redissolved in MeOH and purified by preparative HPLC Method B. This afforded an oil which was treated with HCl in diethyl ether to give a solid material. Recrystallization from acetone and MeOH afforded 75 mg (41%) of the title compound.

出典