Triethylamine → HCID 86712312, compound

HRID 592430Notes

Reaction equation

HRID 592430 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([CH3:14])([CH3:13])[C:10]([NH2:12])=[O:11])#[CH:2].[Cl:15][C:16]1[N:21]=[C:20](Cl)[C:19]([Cl:23])=[CH:18][N:17]=1.CCN(CC)CC>O1CCOCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:15][C:16]1[N:21]=[C:20]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:9]([CH3:14])([CH3:13])[C:10]([NH2:12])=[O:11])[C:19]([Cl:23])=[CH:18][N:17]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 86712311HCID 86712311, compound

Product 1

HCID 86712312HCID 86712312, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-(2-ethynylphenyl)-2-methylpropanamide A36 (0.060 g, 0.32 mmol), 2,4,5-trichloropyrimidine (48 μL, 0.42 mmol) and Et3N (0.18 mL, 1.3 mmol) in 1,4-dioxane (5 mL) was bubbled with N2 for 10 minutes. CuI (0.001 g, 0.006 mmol) and PdCl2(PPh3)2 (0.002 g, 0.003 mmol) were added and the reaction mixture was stirred at room temperature under a N2 atmosphere for 5.5 hours. The volatiles were removed in vacuo and the residue was purified by column chromatography (Biotage Isolera, 12 g SiO2 cartridge, 10-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A37 as an off-white solid (0.067 g, 63%). LCMS-D: rt 3.33 min; m/z 334 [M+H]+.

Workup

  1. customwas bubbled with N2 for 10 minutes
  2. customThe volatiles were removed in vacuo
  3. customthe residue was purified by column chromatography (Biotage Isolera, 12 g SiO2 cartridge, 10-100% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-f5588b614f9a417993e19905452136fc
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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