Hydrochloric Acid → 5-(But-2-ynyloxy)pyrazine-2-carboxylic acid

HRID 1770894

反応式

HRID 1770894 の反応式
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[CH2:11]([OH:15])[C:12]#[C:13][CH3:14].CC(C)([O-])C.[K+].Cl>CN(C=O)C>[CH2:11]([O:15][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1)[C:12]#[C:13][CH3:14]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 129912-Butyn-1-olHCID 4654725-Chloropyrazinoic acidHCID 23665647Potassium tert-butoxide

生成物 1

HCID 584486775-(But-2-ynyloxy)pyrazine-2-carboxylic acid収率 11.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

To a slurry of 5-chloro-pyrazine-2-carboxylic acid (0.79 g, 5.00 mmol) in DMF (35 mL) were added 2-butyn-1-ol (3.74 mL, 50.0 mmol) and potassium tert-butoxide (2.24 g, 20.0 mmol). The resulting mixture was heated at 65° C. overnight. The reaction mixture was neutralized with 2 M HCl and then concentrated in vacuo. A part (400 mg) of the crude material was partitioned between 0.5 M NaOH and a 1:1 mixture of heptane and EtOAc. The aqueous phase was made slightly acidic (pH-3-4) by addition of 1 M HCl. To the obtained suspension was added NaCl(s) and the mixture was extracted twice with EtOAc. The combined organic phases were dried (Na2SO4) and evaporated to give 0.11 g of the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.84 (t, 3H), 5.06 (q, 2H), 8.42 (d, 1H), 8.82 (d, 1H), 13.38 (br. s., 1H); MS (ES+) m/z 193 [M+H]+.

後処理

  1. concentrationconcentrated in vacuo
  2. customA part (400 mg) of the crude material was partitioned between 0.5 M NaOH
  3. additiona 1:1 mixture of heptane and EtOAc
  4. additionby addition of 1 M HCl
  5. additionTo the obtained suspension was added NaCl(s)
  6. extractionthe mixture was extracted twice with EtOAc
  7. dry with materialThe combined organic phases were dried (Na2SO4)
  8. customevaporated

出典と根拠

ORDレコード
ord-989b22ccd2ae4c4f890627cf92dc825b
出典データセット
uspto-grants-2016_02
特許番号
US09248129B2

関連ノート

読み込み中…