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

HRID 656997Notes

Reaction equation

HRID 656997 reaction equation
F[C:2]1[CH:15]=[N:14][C:5]2[N:6]=[CH:7][C:8](=[O:13])[N:9]([CH2:10][CH:11]=[CH2:12])[C:4]=2[CH:3]=1.[CH3:16][O-:17].[Na+].O>CO>[CH3:16][O:17][C:2]1[CH:15]=[N:14][C:5]2[N:6]=[CH:7][C:8](=[O:13])[N:9]([CH2:10][CH:11]=[CH2:12])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium Methoxide2×HCID 689911287-Fluoro-1-(2-propen-1-yl)pyrido[2,3-b]pyrazin-2(1H)-one2×

Product 1

HCID 689936507-(Methyloxy)-1-(2-propen-1-yl)pyrido[2,3-b]pyrazin-2(1H)-oneYield 407.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 7-fluoro-1-(2-propen-1-yl)pyrido[2,3-b]pyrazin-2(1H)-one (196 mg, 0.956 mmol) in MeOH (5 ml) was treated with sodium methoxide (25% w/v in MeOH, 1.03 ml. 4.780 mmol) and stirred at rt for 1 h. The reaction was repeated with more 7-fluoro-1-(2-propen-1-yl)pyrido[2,3-b]pyrazin-2(1H)-one (657 mg, 3.204 mmol) in MeOH (15 ml) and sodium methoxide (25% w/v in MeOH, 3.45 ml. 16.02 mmol). This reaction was also stirred for 1 h after which time both reaction mixtures were combined and treated with water (100 ml). The mixture was then extracted with DCM (3×100 ml). The combined organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give a yellow solid which was purified by column chromatography on silica with ethyl acetate to give the desired product as a brown solid (846 mg, 94%).

Workup

  1. stirringThis reaction was also stirred for 1 h after which time
  2. customboth reaction mixtures
  3. extractionThe mixture was then extracted with DCM (3×100 ml)
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give a yellow solid which
  8. customwas purified by column chromatography on silica with ethyl acetate

Sources & evidence

ORD record
ord-69d4987e1d9a4824ad2b0ab56dfad3d9
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

Loading…