Water → Pyrido(2,3-b)pyrazine-2,3-diol

HRID 1186450Notes

Reaction equation

HRID 1186450 reaction equation
C([O:9][CH2:10][CH3:11])(=O)CC(OCC)=O.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[C:13]=1[NH2:19].[OH2:20]>[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[NH:18]1[C:11](=[O:20])[C:10](=[O:9])[NH:19][C:13]2[N:12]=[CH:17][CH:16]=[CH:15][C:14]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 7761Diethyl MalonateHCID 99562,3-Diaminopyridine

Product 1

HCID 74947Pyrido(2,3-b)pyrazine-2,3-diolYield 80%

Reagents, catalysts & solvents 1

HCID 2733225Ytterbium triflateCatalyst

Conditions

Temperature
80 °C

Procedure

Ytterbium(III) triflate [Yb(OTf)3] (853 mg, 1.38 mmol) and diethyl malonate (7.5 mL, 55.0 mmol) were added to pyridine-2,3-diamine (3.00 g, 27.5 mmol) and the mixture was stirred at 80° C. for 2 hours. After water was added to the reaction mixture, the resulting solid was collected by filtration, washed with ethanol and dried under reduced pressure. Thus, pyrido[3,2-b]pyrazine-2,3(1H,4H)-dione (3.58 g, yield: 80%) was obtained.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with ethanol
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-f1d7472a9981426b837f8b81d0326496
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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