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

HRID 843650Notes

Reaction equation

HRID 843650 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9cfb6ac370e64f39aadf892d79169351
Source dataset
uspto-grants-2002_04
Patent number
US06380204B1

Reaction notes

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