Allyl Isothiocyanate → 1-Allyl-3-(3-phenylpyrido[2,3-b]pyrazin-6-yl)thiourea

HRID 215797Notes

Reaction equation

HRID 215797 reaction equation
[H-].[Na+].[C:3]1([C:9]2[N:14]=[C:13]3[N:15]=[C:16]([NH2:19])[CH:17]=[CH:18][C:12]3=[N:11][CH:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:20]([N:23]=[C:24]=[S:25])[CH:21]=[CH2:22]>CN(C)C=O>[CH2:20]([NH:23][C:24]([NH:19][C:16]1[CH:17]=[CH:18][C:12]2[C:13]([N:15]=1)=[N:14][C:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[CH:10][N:11]=2)=[S:25])[CH:21]=[CH2:22]

Participants

5

Reactant 3

HCID 5971Allyl IsothiocyanateHCID 24758Sodium hydrideHCID 121331983-Phenylpyrido[2,3-b]pyrazin-6-ylamine

Product 1

HCID 114613991-Allyl-3-(3-phenylpyrido[2,3-b]pyrazin-6-yl)thiourea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

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.

Workup

  1. additionadded dropwise
  2. customThe cooling bath is removed
  3. waitthe mixture is left
  4. additionis added dropwise
  5. additionAfter the addition
  6. customthe cooling bath is removed
  7. waitthe mixture is then left
  8. stirringto stir at room temperature for 1.5 hours
  9. additionthe mixture is poured into about 250 ml of distilled water
  10. filtrationthe precipitated orange solid is filtered off with suction
  11. customPurification
  12. customby column chromatography several times (mobile phases dichloromethane/methanol mixtures) and subsequent purification by preparative HPLC
  13. customafford a yellow solid

Sources & evidence

ORD record
ord-cd3f340171ea4a4fac715a60a6ae593e
Source dataset
uspto-grants-2012_06
Patent number
US08193186B2

Reaction notes

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