Methanol → 2-(2-(2-(2,5-Dichloropyrimidin-4-yl)ethyl)phenyl)propanamide

HRID 592415Notes

Reaction equation

HRID 592415 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:16]([CH3:20])[C:17]([NH2:19])=[O:18])[C:5]([Cl:21])=[CH:4][N:3]=1.CO>CN(C=O)C.CCOC(C)=O.[Pt]=O>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:16]([CH3:20])[C:17]([NH2:19])=[O:18])[C:5]([Cl:21])=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 887MethanolHCID 867123062-((2,5-Dichloropyrimidin-4-ylethynyl)phenyl)propanamide

Product 1

HCID 867123072-(2-(2-(2,5-Dichloropyrimidin-4-yl)ethyl)phenyl)propanamide

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(2-((2,5-dichloropyrimidin-4-yl)ethynyl)phenyl)propanamide A29 (1.0 g, 3.1 mmol) in DMF (55 mL) and MeOH (5 mL) was stirred with platinum(II)oxide (0.21 g, 0.94 mmol) under an atmosphere of hydrogen for 120 hours at ambient temperature. The reaction mixture was diluted with EtOAc and filtered through a plug of Celite. The filter cake was washed with EtOAc and the solvents were removed in vacuo to give a crude residue that was purified by silica gel column chromatography (Combiflash Rf, 0-90% EtOAc in cyclohexane), giving the title compound A30 as an off white solid (0.65 g, 64%). LCMS-C: rt 4.98 min; m/z 324 [M+H]+.

Workup

  1. filtrationfiltered through a plug of Celite
  2. washThe filter cake was washed with EtOAc
  3. customthe solvents were removed in vacuo
  4. customto give a crude residue that
  5. customwas purified by silica gel column chromatography (Combiflash Rf, 0-90% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-5b7962be32354250905e185ceb135078
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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