Diisopropylethylamine → 2-[4-(2-Chloro-pyrimidin-5-ylethynyl)-phenyl]-N-ethyl-propionamide

HRID 330826Notes

Reaction equation

HRID 330826 reaction equation
[CH2:1]([NH:3][C:4](=[O:15])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[CH:14])=[CH:9][CH:8]=1)[CH3:6])[CH3:2].[Cl:16][C:17]1[N:22]=[CH:21][C:20](I)=[CH:19][N:18]=1.CCN(C(C)C)C(C)C>C1COCC1.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.[Cu]I>[Cl:16][C:17]1[N:22]=[CH:21][C:20]([C:14]#[C:13][C:10]2[CH:9]=[CH:8][C:7]([CH:5]([CH3:6])[C:4]([NH:3][CH2:1][CH3:2])=[O:15])=[CH:12][CH:11]=2)=[CH:19][N:18]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 17142232-Chloro-5-iodopyrimidineHCID 86669567N-Ethyl-2-(4-ethynyl-phenyl)-propionamide

Product 1

HCID 866695682-[4-(2-Chloro-pyrimidin-5-ylethynyl)-phenyl]-N-ethyl-propionamide

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 1.10 g (5.46 mmol) N-ethyl-2-(4-ethynyl-phenyl)-propionamide (XVII.1) in 10 mL THF are added 1.31 g (5.46 mmol) 2-chloro-5-iodo-pyrimidine under argon, followed by 0.42 g (0.60 mmol) Pd(PPh3)2Cl2 as catalyst, 57 mg (0.30 mmol) copper(I)iodide and 2.1 mL (12 mmol) DIPEA as base. The mixture is stirred at rt for 4 h. After that time, the mixture is filtered and the solvent is evaporated from the filtrate. The residue is purified by column chromatography (silicia gel; DCM:MeOH gradient 1:0/1:1).

Workup

  1. filtrationAfter that time, the mixture is filtered
  2. customthe solvent is evaporated from the filtrate
  3. customThe residue is purified by column chromatography (silicia gel; DCM:MeOH gradient 1:0/1:1)

Sources & evidence

ORD record
ord-3fb5c3261f5545acbc572579b0d6e36a
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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