Methanol → 2-(2-(2-(2-Chloro-5-methylpyrimidin-4-yl)ethyl)phenyl)propanamide

HRID 592446Notes

Reaction equation

HRID 592446 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]([CH3:21])=[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[CH:16]([CH3:20])[C:17]([NH2:19])=[O:18])[C:5]([CH3:21])=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 887MethanolHCID 867123222-(2-((2-Chloro-5-methylpyrimidin-4-yl)ethynyl)phenyl)propanamide

Product 1

HCID 867123232-(2-(2-(2-Chloro-5-methylpyrimidin-4-yl)ethyl)phenyl)propanamide

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalyst2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(2-((2-chloro-5-methylpyrimidin-4-yl)ethynyl)phenyl)propanamide A48 (2.08 g, 6.95 mmol) in DMF (110 mL) and MeOH (10 mL) was stirred with PtO2 (0.395 g, 1.74 mmol) under an atmosphere of H2 for 16 hours at room temperature. An extra portion of PtO2 (0.189 g, 0.832 mmol) was added and stirring was continued under H2 for 72 hours at room temperature. The mixture was diluted with EtOAc (200 mL) and filtered through Celite. The volatiles were removed in vacuo and the residue was purified by column chromatography (Biotage Isolera, 120 g SiO2 cartridge, 10-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A49 as a white solid (1.51 g, 72%). LCMS-D: rt 3.15 min; m/z 304 [M+H]+.

Workup

  1. filtrationfiltered through Celite
  2. customThe volatiles were removed in vacuo
  3. customthe residue was purified by column chromatography (Biotage Isolera, 120 g SiO2 cartridge, 10-100% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-102f9478b1f94d05a1b47ca61640ed57
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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