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

HRID 1035392Notes

Reaction equation

HRID 1035392 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-191e83afff42484fb900996ea9efc940
Source dataset
uspto-grants-2013_10
Patent number
US08546387B2

Reaction notes

Loading…