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

HRID 656947Notes

Reaction equation

HRID 656947 reaction equation
[F: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>[F: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 594373427-Fluoropyrido[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 689911287-Fluoro-1-(2-propen-1-yl)pyrido[2,3-b]pyrazin-2(1H)-oneYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Fluoropyrido[2,3-b]pyrazin-2(1H)-one (306 mg, 1.855 mmol) was suspended in dry DMF (10 mL) under argon at rt, and the stirred suspension was treated with K2CO3 (845 mg, 6.12 mmol) and allyl iodide (223 μl, 2.41 mmol). It was then stirred for 1 h before addition of water (100 ml). The mixture was then extracted with DCM (2×200 ml) and 5% MeOH/DCM (100 ml). The combined organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated and purified by column chromatography on silica with a 0-10% MeOH in DCM gradient to give the desired product as a yellow solid (177 mg, 47%).

Workup

  1. extractionThe mixture was then extracted with DCM (2×200 ml) and 5% MeOH/DCM (100 ml)
  2. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by column chromatography on silica with a 0-10% MeOH in DCM gradient

Sources & evidence

ORD record
ord-5616d03f3b1249faafb55c1ab0461207
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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