Diisopropylethylamine → N-(1-(4-((2-Chloropyrimidin-5-yl)ethynyl)phenyl)propan-2-yl)acetamide

HRID 76175Notes

Reaction equation

HRID 76175 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:5][CH:4]=1)#[CH: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:2]#[C:1][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:5][CH:4]=2)=[CH:19][N:18]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 17142232-Chloro-5-iodopyrimidineHCID 86669621N-(1-(4-ethynylphenyl)propan-2-yl)acetamide

Product 1

HCID 86669620N-(1-(4-((2-Chloropyrimidin-5-yl)ethynyl)phenyl)propan-2-yl)acetamide

Reagents, catalysts & solvents 3

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

Procedure

To 1.20 g (5.96 mmol) N-(1-(4-ethynylphenyl)propan-2-yl)acetamide (I58.3) in 10 mL THF are added 1.43 g (5.96 mmol) 2-chloro-5-iodopyrimidine, 418 mg (0.60 mmol) bis(triphenylphosphine)dichloropalladium, 56.8 mg (0.30 mmol) CuI and 2.03 mL (11.9 mmol) DIPEA. The reaction mixture is stirred at r.t. for 4 h. The solvent is removed in vacuo and the residue is purified by column chromatography (silica gel, DCM/MeOH 98/2).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by column chromatography (silica gel, DCM/MeOH 98/2)

Sources & evidence

ORD record
ord-46fcc49cedba4ca8b974c995b841e672
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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