Methanol → 2-(2-(2-(2-((6-Methoxypyridin-3-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamide

HRID 592473Notes

Reaction equation

HRID 592473 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14]([C:16]#[C:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH:24]([CH3:28])[C:25]([NH2:27])=[O:26])[C:13]([C:29]([F:32])([F:31])[F:30])=[CH:12][N:11]=2)=[CH:5][CH:4]=1.CO>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH:24]([CH3:28])[C:25]([NH2:27])=[O:26])[C:13]([C:29]([F:31])([F:32])[F:30])=[CH:12][N:11]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 867123412-(2-((2-((6-Methoxypyridin-3-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)phenyl)propanamide

Product 1

HCID 732954642-(2-(2-(2-((6-Methoxypyridin-3-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamideYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(2-((2-((6-methoxypyridin-3-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)phenyl)propanamide A69 (0.198 g, 0.449 mmol) in EtOAc (20 mL) and MeOH (10 mL) was stirred over 10% Pd/C (wetted with ca. 53% water, 0.150 g) under an atmosphere of hydrogen for 16 hours. The mixture was filtered through Celite and the solvent was removed in vacuo. Purification by column chromatography (Biotage Isolera, 40 g SiO2, 0-80% EtOAc in petroleum benzine 40-60° C.) gave the title compound 61 as a white solid (0.126 g, 63%). LCMS-D: rt 3.43 min; m/z 446 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe solvent was removed in vacuo
  3. customPurification by column chromatography (Biotage Isolera, 40 g SiO2, 0-80% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-ed82b74b86614b72a2c30dcaf8dc21d6
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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