Triethylamine → 2-((2,5-Dichloropyrimidin-4-ylethynyl)phenyl)propanamide

HRID 592414Notes

Reaction equation

HRID 592414 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([CH3:13])[C:10]([NH2:12])=[O:11])#[CH:2].[Cl:14][C:15]1[N:20]=[C:19](Cl)[C:18]([Cl:22])=[CH:17][N:16]=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:14][C:15]1[N:20]=[C:19]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[CH:9]([CH3:13])[C:10]([NH2:12])=[O:11])[C:18]([Cl:22])=[CH:17][N:16]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 867122792-(2-Ethynylphenyl)propanamide

Product 1

HCID 867123062-((2,5-Dichloropyrimidin-4-ylethynyl)phenyl)propanamide

Reagents, catalysts & solvents 3

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

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(2-ethynylphenyl)propanamide K7 (2.5 g, 14 mmol) and 2,4,5-trichloropyrimidine (2.2 mL, 19 mmol) in 1,4-dioxane (27 mL) and Et3N (8.1 mL, 58 mmol) containing CuI (0.055 g, 0.29 mmol) was added PdCl2(PPh3)2 (0.10 g, 0.14 mmol). The reaction mixture was heated at 60° C. for 2.5 hours under a nitrogen atmosphere. The solvent was removed in vacuo and the residue was diluted with 20% Et2O in cyclohexane. The precipitate was filtered, washed with water and dried in vacuo to give the title compound A29 as a light brown solid (4.52 g, 98%). LCMS-C: rt 5.10 min; m/z 320 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with 20% Et2O in cyclohexane
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-9bdf6096684a4b3a9ef190a863c303b5
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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