3-[2-(methylthio)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-N-[3-(trifluoromethyl)phenyl]benzamide → 3-(7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-N-[3-(trifluoromethyl)phenyl]benzamide

HRID 338747Notes

Reaction equation

HRID 338747 reaction equation
CS[C:3]1[N:4]=[CH:5][C:6]2[CH2:12][N:11]([C:13]3[CH:14]=[C:15]([CH:29]=[CH:30][CH:31]=3)[C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)=[O:17])[CH2:10][CH2:9][C:7]=2[N:8]=1>C(O)C.[Ni]>[N:8]1[C:7]2[CH2:9][CH2:10][N:11]([C:13]3[CH:14]=[C:15]([CH:29]=[CH:30][CH:31]=3)[C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:27])([F:26])[F:28])[CH:20]=3)=[O:17])[CH2:12][C:6]=2[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 1

HCID 717356913-[2-(methylthio)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-N-[3-(trifluoromethyl)phenyl]benzamide

Product 1

HCID 717361713-(7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-N-[3-(trifluoromethyl)phenyl]benzamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A suspension of 3-[2-(methylthio)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-N-[3-(trifluoromethyl)phenyl]benzamide 3 (150 mg, 0.337 mmol) in ethanol (15 ml) was treated with Raney Nickel (˜150 mg, slurry in water) and the reaction mixture was stirred under 1 atm. H2 at 60° C. for 18 hours. The catalyst was filtered off (celite) and the filtrate was concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, EtOAc) gave the title compound as a yellow oil which solidified to a glass (84 mg, 63%).

Workup

  1. filtrationThe catalyst was filtered off (celite)
  2. concentrationthe filtrate was concentrated
  3. washElution through a flash column (silica gel 60, 230-400 mesh, EtOAc)

Sources & evidence

ORD record
ord-c253c00c8b02488599cf513149f9fdad
Source dataset
uspto-grants-2014_11
Patent number
US08889870B2

Reaction notes

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