Ethyl orthoformate → ethyl [5-(1H-tetrazol-1-yl)pyrazin-2-yl]acetate

HRID 2173331ノート

反応式

HRID 2173331 の反応式
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:6][CH:7]=1.[CH:14](OCC)(OCC)OCC.[N-:24]=[N+:25]=[N-:26].[Na+]>CC(O)=O>[N:1]1([C:2]2[N:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:6][CH:7]=2)[CH:14]=[N:26][N:25]=[N:24]1

参加物

5

反応物 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 72212710Ethyl 2-(5-aminopyrazin-2-YL)acetate

生成物 1

HCID 77230648ethyl [5-(1H-tetrazol-1-yl)pyrazin-2-yl]acetate

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

A solution of the ethyl (5-aminopyrazin-2-yl)acetate (2.0 g, 11.0 mmol) and triethyl orthoformate (4.9 g, 33.1 mmol) in 60 mL of HOAc was added sodium azide (0.9 g, 13.8 mmol) and heated to 100° C. for 1 hour. The reaction was completed which was checked by TLC. The reaction mixture was cooled to r.t. The solvent was removed under vacuum. The residue was dissolved in EtOAc, washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatograph to afford the product ethyl [5-(1H-tetrazol-1-yl)pyrazin-2-yl]acetate. 1H-NMR (400 MHz, CDCl3) δ ppm 9.50 (s, 1H), 9.35 (s, 1H), 8.54 (s, 1H), 4.21 (q, J=7.2 Hz, 2H), 3.98 (s, 2H), 1.27 (t, J=7.2 Hz, 3H).

後処理

  1. temperatureThe reaction mixture was cooled to r.t
  2. customThe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatograph

出典と根拠

ORDレコード
ord-cc417bf4702c443c9250bd76e81d6441
出典データセット
uspto-grants-2015_06
特許番号
US09056859B2

反応ノート

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