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

HRID 1035391Notes

Reaction equation

HRID 1035391 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)=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1.[C:24](OCC)(=[O:30])[C:25](OCC)=[O:26]>>[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([O:9][C:6]2[C:7]3[NH:8][C:25](=[O:26])[C:24](=[O:30])[NH:1][C:2]=3[N:3]=[CH:4][CH:5]=2)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 42625416Tert-butyl 4-(2,3-diaminopyridin-4-yloxy)phenylcarbamate

Product 1

HCID 595888448-(4-aminophenoxy)pyrido[2,3-b]pyrazine-2,3(1H,4H)-dioneYield 25%

Procedure

A solution of tert-butyl 4-(2,3-diamino pyridin-4-yloxy)phenylcarbamate (0.320 g, 1.0 mmol) in diethyl oxalate (2 ml) is reacted twice for 10 minutes in a microwave reactor (180 C, 150 W). The solution is cooled and the solid filtered and washed with cold ethanol. Obtained 8-(4-aminophenoxy)pyrido[2,3-b]pyrazine-2,3(1H,4H)-dione (70 mg, 25% yield) as a grey solid.

Workup

  1. temperatureThe solution is cooled
  2. filtrationthe solid filtered
  3. washwashed with cold ethanol

Sources & evidence

ORD record
ord-19b96df924f5431cbe3f408a1565a212
Source dataset
uspto-grants-2013_10
Patent number
US08546387B2

Reaction notes

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