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Ammonium formate → 6-fluoro-3-(2-methyl-pyridin-3-yl)-2-[2-(2-methyl-thiazol-4-yl)-ethyl]-3H-quinazolin-4-one

HRID 843650
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HRID 843650 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]=[CH:13][C:14]1[N:15]=[C:16]([CH3:19])[S:17][CH:18]=1)[N:6]([C:20]1[C:21]([CH3:26])=[N:22][CH:23]=[CH:24][CH:25]=1)[C:5]2=[O:27].C([O-])=O.[NH4+]>[Pd].CO>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH2:13][C:14]1[N:15]=[C:16]([CH3:19])[S:17][CH:18]=1)[N:6]([C:20]1[C:21]([CH3:26])=[N:22][CH:23]=[CH:24][CH:25]=1)[C:5]2=[O:27]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 498262226-fluoro-3-(2-methyl-pyridin-3-yl)-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3H-quinazolin-4-one

생성물 1

HCID 226116916-fluoro-3-(2-methyl-pyridin-3-yl)-2-[2-(2-methyl-thiazol-4-yl)-ethyl]-3H-quinazolin-4-one수율 47%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

To a slurry of 10% palladium on carbon (0.15 g) in methanol(12 mL) were added 6-fluoro-3-(2-methyl-pyridin-3-yl)-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3 H-quinazolin-4-one (0.075 g, 0.198 mmol) and ammonium formate (1.2 g, 19 mmol). The mixture was refluxed overnight, cooled and filtered through celite. The pad was washed with methanol. The filtrate was concentrated. The residue was partitioned between chloroform and water. The phases were separated and the aqueous layer was extracted with chloroform. The combined organic phase was washed with water and brine, dried over magnesium sulfate, and concentrated to afford 0.035 g (47%) of 6-fluoro-3-(2-methyl-pyridin-3-yl)-2-[2-(2-methyl-thiazol-4-yl)-ethyl]-3H-quinazolin-4-one as a white solid.

후처리

  1. temperatureThe mixture was refluxed overnight
  2. temperaturecooled
  3. filtrationfiltered through celite
  4. washThe pad was washed with methanol
  5. concentrationThe filtrate was concentrated
  6. customThe residue was partitioned between chloroform and water
  7. customThe phases were separated
  8. extractionthe aqueous layer was extracted with chloroform
  9. washThe combined organic phase was washed with water and brine
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9cfb6ac370e64f39aadf892d79169351
출처 데이터셋
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06380204B1

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