Ammonium Hydroxide → Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate

HRID 990711Notes

Reaction equation

HRID 990711 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:12]([CH3:13])=[CH:11][N:10]=[C:9](O)[C:8]1=[O:15])=[O:5])[CH3:2].P(Br)(Br)([Br:18])=O.[NH4+].[OH-]>C(Cl)(Cl)Cl>[Br:18][C:9]1[C:8](=[O:15])[N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:12]([CH3:13])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24613Phosphorus oxybromideHCID 178472615HCID 178472615, compound

Product 1

HCID 1514288Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A stirred slurry of 505 mg (2.38 mmol) of 1-(ethoxycarbonyl-methyl)-3-hydroxy-6-methylpyrazinone and 756 mg (2.64 mmol) of phosphorous oxybromide in 1.7 ml of CHCl3 was stirred at 50° C. under a slow stream of Ar for 1.5 h, then allowed to cool to rt overnight. The reaction mixture was diluted with CHCl3 and ice water, basified with NH4OH, and extracted with CHCl3. The combined organic layers were dried over Na2SO4, treated with activated carbon, filtered and concentrated to give 2-5 as an orange colored solid: 1H NMR (CDCl3) δ7.06 (s, 1H), 4.77 (s, 2H), 4.27 (q, 2H, 7.2 Hz), 2.24 (s, 3H), 1.31 (t, 3H, 7.2 Hz).

Workup

  1. extractionextracted with CHCl3
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. additiontreated with activated carbon
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fce419494014425188b09ebe29bceaba
Source dataset
uspto-grants-2002_10
Patent number
US06462050B1

Reaction notes

Loading…