反応 #1265379

反応方程式

3-phenylpyrido[2,3-b]pyrazin-6-ylamine

allyl isothiocyanate

sodium hydride

→

1-allyl-3-(3-phenylpyrido[2,3-b]pyrazin-6-yl)thiourea

溶媒

dimethylformamide

dimethylformamide

dimethylformamide

反応条件

後処理

1. 1
   workup.ADDITIONadded dropwise
2. 2
   その他The cooling bath is removed
3. 3
   workup.WAITthe mixture is left
4. 4
   workup.ADDITIONis added dropwise
5. 5
   workup.ADDITIONAfter the addition
6. 6
   その他the cooling bath is removed
7. 7
   workup.WAITthe mixture is then left
8. 8
   workup.STIRRINGto stir at room temperature for 1.5 hours
9. 9
   workup.ADDITIONthe mixture is poured into about 250 ml of distilled water
10. 10
    ろ過the precipitated orange solid is filtered off with suction
11. 11
    その他Purification
12. 12
    その他by column chromatography several times (mobile phases dichloromethane/methanol mixtures) and subsequent purification by preparative HPLC
13. 13
    その他afford a yellow solid

実験手順

0.246 g of sodium hydride (6.14 mmol) is introduced into 5 ml of anhydrous dimethylformamide under nitrogen as protective gas. The mixture is cooled to 0° C. in an ice bath. 1.05 g of 3-phenylpyrido[2,3-b]pyrazin-6-ylamine (4.72 mmol) are dissolved in 5 ml of anhydrous dimethylformamide and added dropwise. The cooling bath is removed, and the mixture is left to stir at RT for 30 minutes. The mixture is then cooled to 0° C. again in the ice bath, and 0.469 g of allyl isothiocyanate (4.72 mmol), dissolved in 4 ml of anhydrous dimethylformamide, is added dropwise. After the addition is complete, the cooling bath is removed, and the mixture is then left to stir at room temperature for 1.5 hours. For working up, the mixture is poured into about 250 ml of distilled water, and the precipitated orange solid is filtered off with suction. Purification by column chromatography several times (mobile phases dichloromethane/methanol mixtures) and subsequent purification by preparative HPLC afford a yellow solid.

出典