Hydrochloric Acid → 5-(pyrimidin-2-yl)pyridin-2(1H)-one

HRID 525405노트

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HRID 525405 반응식
F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[O:14]1CCOCC1.Cl>O>[N:9]1[CH:10]=[CH:11][CH:12]=[N:13][C:8]=1[C:5]1[CH:4]=[CH:3][C:2](=[O:14])[NH:7][CH:6]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 578217612-(6-Fluoropyridin-3-yl)pyrimidine

생성물 1

HCID 580164905-(pyrimidin-2-yl)pyridin-2(1H)-one수율 53%

시약·촉매·용매 1

HCID 962Water용매

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온도
100 °C

실험 절차

A resealable tube was charged with 2-(6-fluoropyridin-3-yl)pyrimidine (0.150 g, 0.856 mmol), dioxane (3.0 mL), and water (1.00 mL). Concentrated hydrochloric acid (37%)(0.25 mL) was added, the system was flushed with argon, the tube was sealed, and the reaction mixture stirred at 100° C. for 1.5 hours. The reaction mixture was then partitioned between EtOAc and saturated aqueous NaHCO3 solution. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 5-(pyrimidin-2-yl)pyridin-2(1H)-one (0.079 g, 0.456 mmol, 53% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.45 (dd, J=9.59, 0.78 Hz, 1H), 7.33 (t, J=4.89 Hz, 1H), 8.32 (td, J=10.07, 2.35 Hz, 2H), 8.79 (d, J=4.89 Hz, 2H), 11.96 (br. s., 1H). m/z (ESI) 174 (M+H)+.

후처리

  1. customthe system was flushed with argon
  2. customthe tube was sealed
  3. customThe reaction mixture was then partitioned between EtOAc and saturated aqueous NaHCO3 solution
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1f3bafc158c3497e9bd4626b237f5361
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340549B2

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