Diethyl Oxalate → 8-(4-Amino-3-fluorophenoxy)pyrido[3,2-b]pyrazine-2,3(1H,4H)-dione

HRID 217801Notes

Reaction equation

HRID 217801 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16]C(=O)OC(C)(C)C)=[C:12]([F:24])[CH:11]=2)[CH:5]=[CH:4][N:3]=1.[C:25](OCC)(=[O:31])[C:26](OCC)=[O:27]>CCO>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:6]2[C:7]3[NH:8][C:25](=[O:31])[C:26](=[O:27])[NH:1][C:2]=3[N:3]=[CH:4][CH:5]=2)=[CH:11][C:12]=1[F:24]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 44185833tert-Butyl (4-((2,3-diaminopyridin-4-yl)oxy)-2-fluorophenyl)carbamate

Product 1

HCID 595888758-(4-Amino-3-fluorophenoxy)pyrido[3,2-b]pyrazine-2,3(1H,4H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 4-(2,3-diaminopyridin-4-yloxy)-2-fluorophenylcarbamate (1.03 g, 3.08 mmol) was dissolved in dry EtOH (10 mL), diethyl oxalate (10 mL) was added and the solution was heated to reflux for 96 h, cooled to RT and filtered. The title compound was isolated as a white solid. Yield: 820 mg (92%).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 96 h
  3. filtrationfiltered

Sources & evidence

ORD record
ord-0c6336a0cbf74d0190298aeab48f1b8c
Source dataset
uspto-grants-2012_06
Patent number
US08198279B2

Reaction notes

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