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

HRID 539284

반응식

HRID 539284 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, 3 H), 5.06 (q, 2 H), 8.42 (d, 1 H), 8.82 (d, 1 H), 13.38 (br. s., 1 H); 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-8b38c90e69884010bcdd2ff862d3f590
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865911B2

연결된 노트

불러오는 중…