HCID 86712312, compound → HCID 86712313, compound

HRID 592431Notes

Reaction equation

HRID 592431 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[C:16]([CH3:21])([CH3:20])[C:17]([NH2:19])=[O:18])[C:5]([Cl:22])=[CH:4][N:3]=1>CO.CN(C=O)C.CCOC(C)=O.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[C:16]([CH3:20])([CH3:21])[C:17]([NH2:19])=[O:18])[C:5]([Cl:22])=[CH:4][N:3]=1

Participants

6

Reactant 1

HCID 86712312HCID 86712312, compound

Product 1

HCID 86712313HCID 86712313, compound

Reagents, catalysts & solvents 4

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(2-((2,5-dichloropyrimidin-4-yl)ethynyl)phenyl)-2-methylpropanamide A37 (0.067 g, 0.20 mmol) and PtO2 (0.014 g, 0.060 mmol) in MeOH (3.0 mL) and DMF (3.0 mL) was stirred in an atmosphere of H2 for 64 hours. The mixture was diluted with EtOAc, filtered through Celite and the filtrate solvent was removed in vacuo. The residue was purified by column chromatography (Biotage Isolera, 12 g SiO2, 0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A38 as an off-white solid (0.042 g, 62%). LCMS-D: rt 3.37 min; m/z 338 [M+H]+.

Workup

  1. filtrationfiltered through Celite
  2. customthe filtrate solvent was removed in vacuo
  3. customThe residue was purified by column chromatography (Biotage Isolera, 12 g SiO2, 0-100% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-34e878b793834a49b4d2f2292dba12a7
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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