Potassium Carbonate → 5-Methyl-6-carboethoxy-7-amino-1H-pyrrolo[2,3-b]pyrazine

HRID 235071

反応式

HRID 235071 の反応式
Cl[C:2]1[C:7]([C:8]#[N:9])=[N:6][CH:5]=[CH:4][N:3]=1.Cl.[CH2:11]([O:13][C:14](=[O:18])[CH2:15][NH:16][CH3:17])[CH3:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:17][N:16]1[C:2]2[N:3]=[CH:4][CH2:5][NH:6][C:7]=2[C:8]([NH2:9])=[C:15]1[C:14]([O:13][CH2:11][CH3:12])=[O:18]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 2924653-Chloropyrazine-2-carbonitrile

生成物 1

HCID 702867985-Methyl-6-carboethoxy-7-amino-1H-pyrrolo[2,3-b]pyrazine収率 31.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Chloro-3-cyanopyrazine (0.808 g, 5.79 mmol), prepared by the method of Shneller, et. al., J. Het. Chem., 12:513 (1975), was dissolved in 30 ml DMF under nitrogen and treated with sarcosine ethyl ester hydrochloride (0.978 g, 6.37 mmol) followed by K2CO3 (1.68 g, 12.16 mmol) at rt. The reaction mixture was gently refluxed for 36 h after which the cooled solution was partitioned between water and CHCl3. The aqueous phase was extracted with CHCl3 and the combined organics washed with water then brine and dried over Na2SO4. Concentration gave a green-black oil that was purified by chromatography on silica gel eluting with a gradient from 3:1 to 1:1 hexanes:ethyl acetate to give 0.40 g (31%) of the title compound as an orange solid. mp: 119°-121° C. 1H NMR (300 MHz, CDCl3) δ1.47 (t, 3H), 4.01 (s, 3H), 4.46 (q, 2H), 5.65 (br s, 2H), 8.32 (d, 1H), 8.38 (d, 1H). MS (DCI/NH3) m/e 220 (M+H)+. Analysis calc'd. for C10H12N4O2: C, 54.54; H, 5.49; N, 25.44; Found: C, 54.29; H, 5.52; N, 25.42.

後処理

  1. temperatureThe reaction mixture was gently refluxed for 36 h after which the cooled solution
  2. customwas partitioned between water and CHCl3
  3. extractionThe aqueous phase was extracted with CHCl3
  4. washthe combined organics washed with water
  5. dry with materialbrine and dried over Na2SO4
  6. concentrationConcentration
  7. customgave a green-black oil that
  8. customwas purified by chromatography on silica gel eluting with a gradient from 3:1 to 1:1 hexanes

出典と根拠

ORDレコード
ord-b18925ec9ba347d5ba4ee2e741c06ddf
出典データセット
uspto-grants-1997_01
特許番号
US05597823

関連ノート

読み込み中…