Water → 7-bromo-1-(2-propen-1-yl)pyrido[2,3-b]pyrazin-2(1H)-one

HRID 656932Notes

Reaction equation

HRID 656932 reaction equation
[Br:1][C:2]1[CH:12]=[N:11][C:5]2[N:6]=[CH:7][C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19](I)[CH:20]=[CH2:21].O>CN(C=O)C>[Br:1][C:2]1[CH:12]=[N:11][C:5]2[N:6]=[CH:7][C:8](=[O:10])[N:9]([CH2:21][CH:20]=[CH2:19])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 57815479HCID 57815479, compound

Product 1

HCID 688205297-bromo-1-(2-propen-1-yl)pyrido[2,3-b]pyrazin-2(1H)-oneYield 64.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Bromopyrido[2,3-b]pyrazin-2(1H)-one (368 mg, 1.628 mmol) was suspended in dry DMF (10 ml) under argon at rt, and the stirred suspension was treated with K2CO3 (741 mg, 5.372 mmol) and allyl iodide (331 μL, 3.581 mmol). It was then stirred for 2 h before addition of water (100 ml). The mixture was then extracted with DCM (3×200 ml). The DCM extracts were combined, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give a brown solid which was purified by column chromatography on silica with a 0-10% MeOH in DCM gradient to give the desired product as a light brown solid (278 mg, 64%).

Workup

  1. extractionThe mixture was then extracted with DCM (3×200 ml)
  2. dry with materialdried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto give a brown solid which
  6. customwas purified by column chromatography on silica with a 0-10% MeOH in DCM gradient

Sources & evidence

ORD record
ord-be5a1bbfa7d647e38c26cfa30123b902
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

Loading…