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

HRID 1770894

반응식

HRID 1770894 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-989b22ccd2ae4c4f890627cf92dc825b
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09248129B2

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