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

HRID 657103ノート

反応式

HRID 657103 の反応式
[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

参加物

5

反応物 2

HCID 11430Potassium CarbonateHCID 68811995Ethyl N-[2-{[2,2-bis(methyloxy)ethyl]amino}-6-(methyloxy)-3-pyridinyl]glycinate

生成物 1

HCID 533021904-(2,2-Dimethoxyethyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
107.5 °C

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-9f3f64550bf3448c8e30332335be23d9
出典データセット
uspto-grants-2011_12
特許番号
US08071592B2

反応ノート

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