Potassium Carbonate → 4-(2,2-Dimethoxyethyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 657103Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:21][CH3:22])[CH2:4][NH:5][C:6]1[C:11]([NH:12][CH2:13][C:14](OCC)=[O:15])=[CH:10][CH:9]=[C:8]([O:19][CH3:20])[N:7]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O=[Mn]=O>[CH3:1][O:2][CH:3]([O:21][CH3:22])[CH2:4][N:5]1[C:14](=[O:15])[CH:13]=[N:12][C:11]2[CH:10]=[CH:9][C:8]([O:19][CH3:20])=[N:7][C:6]1=2

Participants

Conditions

Temperature: 107.5 °C

Procedure

A mixture of ethyl N-[2-{[2,2-bis(methyloxy)ethyl]amino}-6-(methyloxy)-3-pyridinyl]glycinate (1 g, 3.2 mmol) and potassium carbonate (1.3 g, 9.6 mmol) in DMF (64 mL, 0.05M) was heated at 105-110° C. for 2 h. The mixture was cooled to room temperature and MnO2 (0.8 g, 11 mmol) was added and the reaction was stirred for 18 h. The reaction was filtered, concentrated, and the residue was dissolved in ethyl acetate and washed with water. The organic extract was concentrated and added to a silica column which was then eluted with 0-100% ethyl acetate in hexane affording the desired compound (0.78 g, 78%).

Workup

temperatureThe mixture was cooled to room temperature
filtrationThe reaction was filtered
concentrationconcentrated
dissolutionthe residue was dissolved in ethyl acetate
washwashed with water
extractionThe organic extract
concentrationwas concentrated
additionadded to a silica column which
washwas then eluted with 0-100% ethyl acetate in hexane affording the desired compound (0.78 g, 78%)

Sources & evidence

ORD record: ord-9f3f64550bf3448c8e30332335be23d9
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071592B2

Reaction notes

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