HCID 68985826, compound → HCID 69297923, compound

HRID 1930289Notes

Reaction equation

HRID 1930289 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[C:20](=[O:21])[N:19]([CH3:22])[C:12]3[N:13]=[C:14](SC)[N:15]=[CH:16][C:11]=3[CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]>CCO.[Ni].O>[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[C:20](=[O:21])[N:19]([CH3:22])[C:12]3[N:13]=[CH:14][N:15]=[CH:16][C:11]=3[CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 1

HCID 68985826HCID 68985826, compound

Product 1

HCID 69297923HCID 69297923, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of Example A3 (2.5 g, 7.9 mmol) in EtOH (30 ml) was treated with Raney Nickel® (50% slurry in water, 10 g, 85 mmol) and the mixture was refluxed for 3 h. The cooled reaction was filtered and the filtrate was concentrated to give the crude product, which was washed with cold MeOH (2 mL) to give 6-(3-amino-4-fluoro-phenyl)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (1.0 g, 47% yield). 1H NMR (300 MHz, DMSO-d6)δ 9.10 (s, H), 9.07 (s, 1 H), 8.06 (s, 1 H), 7.14 (dd, J=8.7, 2.1 Hz, 1 H), 7.05 (dd, J=11.4, 8.4 Hz, 1 H), 6.82 (m, 1 H), 5.22 (s, 2 H), 3.68 (s, 3 H); MS (ESI) m/z: 271.3 (M+H+).

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. customThe cooled reaction
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated
  5. customto give the crude product, which
  6. washwas washed with cold MeOH (2 mL)

Sources & evidence

ORD record
ord-bb406dcd2a1b42c7a7d711226667a548
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

Loading…