Ethyl pyruvate → 3,6-Dimethyl-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

HRID 21534

Reaction equation

HRID 21534 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[C:10](OCC)(=[O:14])[C:11]([CH3:13])=O>COCCOC>[CH3:13][CH:11]1[NH:1][C:2]2[C:7](=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=2)[NH:8][C:10]1=[O:14]

Participants

4

Reactant 2

HCID 12041Ethyl pyruvateHCID 27344206-Methylpyridine-2,3-diamine

Product 1

HCID 199328033,6-Dimethyl-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-oneYield 58%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2,3-Diamino-6-methylpyridine (3.0 g, 0.024 mol) and 3.2 ml (0.028 mol) of ethyl pyruvate were heated under reflux in 100 ml of 1,2-dimethoxyethane for 4 h. The resulting precipitate (3.9 g) of 3,6-dimethyl-1,4,5-triazanaphthalen-2(1H)-one was filtered off with suction, dried and used directly for the hydrogenation. A reaction analogous to that described for Example 1 resulted in 2.27 g (58%) of the desired compound of melting point 203°-205° C.

Workup

  1. filtrationThe resulting precipitate (3.9 g) of 3,6-dimethyl-1,4,5-triazanaphthalen-2(1H)-one was filtered off with suction
  2. customdried
  3. customA reaction analogous to

Sources & evidence

ORD record
ord-130937875af046e9b9886e946119575a
Source dataset
uspto-grants-1995_06
Patent number
US05424311

Linked notes

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