Reaction #1265379

Reaction equation

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

allyl isothiocyanate

sodium hydride

→

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

Solvents

dimethylformamide

dimethylformamide

dimethylformamide

Conditions

Workup

1. 1
   workup.ADDITIONadded dropwise
2. 2
   OtherThe 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
   Otherthe 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
    Filtrationthe precipitated orange solid is filtered off with suction
11. 11
    OtherPurification
12. 12
    Otherby column chromatography several times (mobile phases dichloromethane/methanol mixtures) and subsequent purification by preparative HPLC
13. 13
    Otherafford a yellow solid

Procedure

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.

Source