Dimethylformamide → t-butyl 5-((E)-2-dimethylaminovinyl)pyrazine-2-carboxylate

HRID 1429630

反応式

HRID 1429630 の反応式
[CH3:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[N:6][CH:7]=1.[CH3:15][N:16]([CH:18]=O)[CH3:17].COC(OC)N(C)C>CCOC(C)=O>[CH3:15][N:16]([CH3:18])/[CH:17]=[CH:1]/[C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 57475683t-Butyl 5-methylpyrazine-2-carboxylate

生成物 1

HCID 57475684t-butyl 5-((E)-2-dimethylaminovinyl)pyrazine-2-carboxylate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

A mixture of t-butyl 5-methylpyrazine-2-carboxylate (1.35 g), DMF (25 mL) and N,N-dimethylformamide dimethylacetal (25 mL) was stirred at 130° C. for 5 h. The reaction solution was cooled to RT and diluted with EtOAc. The mixture was washed with a saturated NaCl solution three times. The organic layer was dried over anhydrous MgSO4, and the insoluble matter was separated by filtration. The filtrate was concentrated and the residue was purified by silica gel column chromatography to obtain the title compound (648 mg). 1H-NMR (CDCl3) δ (ppm): 1.63 (s, 9H), 3.00 (s, 6H), 5.16 (d, J=12.8 Hz, 1H), 7.72 (d, J=12.8 Hz, 1 H), 8.16 (d, J=1.2 Hz, 1H), 8.81 (d, J=1.6 Hz, 1H).

後処理

  1. temperatureThe reaction solution was cooled to RT
  2. washThe mixture was washed with a saturated NaCl solution three times
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. customthe insoluble matter was separated by filtration
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-11f0504771a747e79eb33b206549c666
出典データセット
uspto-grants-2015_01
特許番号
US08940734B2

関連ノート

読み込み中…