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

HRID 76176Notes

Reaction equation

HRID 76176 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]=[C:21](Cl)[CH:20]=[CH:19][N:18]=1>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>[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

5

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 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 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 3.30 g (16.4 mmol) N-(1-(4-ethynylphenyl)propan-2-yl)acetamide (I58.3) in 40 mL THF are added 2.44 g (16.4 mmol) 2,4-dichloropyrimidine, 57.5 mg (82.0 μmol) bis(triphenyphosphine)dichloropalladium and 9.10 mL (65.7 mmol) TEA. The reaction mixture is stirred under reflux for 4 h and at r.t. over night. The reaction mixture is filtrated and the solvent is removed in vacuo. The residue is triturated with water and afterwards with diethylether.

Workup

  1. filtrationThe reaction mixture is filtrated
  2. customthe solvent is removed in vacuo
  3. customThe residue is triturated with water and afterwards with diethylether

Sources & evidence

ORD record
ord-1ca31ebaf67849aa85c3b70296502762
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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