1-(2-((2-Chloro-5-methylpyrimidin-4-yl)ethynyl)phenyl)cyclopropanecarboxamide → 1-(2-(2-(2-Chloro-5-methylpyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

HRID 592434Notes

Reaction equation

HRID 592434 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]2([C:19]([NH2:21])=[O:20])[CH2:18][CH2:17]2)[C:5]([CH3:22])=[CH:4][N:3]=1>CO.CN(C=O)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[C:16]2([C:19]([NH2:21])=[O:20])[CH2:18][CH2:17]2)[C:5]([CH3:22])=[CH:4][N:3]=1

Participants

5

Reactant 1

HCID 867123141-(2-((2-Chloro-5-methylpyrimidin-4-yl)ethynyl)phenyl)cyclopropanecarboxamide

Product 1

HCID 867123151-(2-(2-(2-Chloro-5-methylpyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-((2-chloro-5-methylpyrimidin-4-yl)ethynyl)phenyl)cyclopropanecarboxamide A39 (1.85 g, 5.93 mmol) and PtO2 (0.404 g, 1.78 mmol) in MeOH (10 mL) and DMF (40 mL) was stirred under an atmosphere of H2 for 110 hours at room temperature. The mixture was filtered through Celite and the volatiles were removed in vacuo. The residue was purified by column chromatography (Biotage Isolera, 40 g SiO2, 0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A40 as a white solid (1.65 g, 88%). LCMS-D: rt 3.20 min; m/z 316 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe volatiles were removed in vacuo
  3. customThe residue was purified by column chromatography (Biotage Isolera, 40 g SiO2, 0-100% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-e604d30d5f0e42f3b78000bc73444940
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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