Trimethylsilylacetylene → 2,4-Dichloro-5-((trimethylsilyl)ethynyl)pyrimidine

HRID 1484912Notes

Reaction equation

HRID 1484912 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5](I)=[CH:4][N:3]=1.[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])#[CH:11]>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:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:11]#[C:10][Si:12]([CH3:15])([CH3:14])[CH3:13])=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 2634382,4-Dichloro-5-iodopyrimidine

Product 1

HCID 210809892,4-Dichloro-5-((trimethylsilyl)ethynyl)pyrimidineYield 56%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
35 °C

Procedure

Under nitrogen atmosphere, a mixture of 2,4-dichloro-5-iodopyrimidine (2.0 g, 7.3 mmol, 1.0 eq), Pd(PPh3)2Cl2 (256 mg, 0.37 mmol, 0.05 eq), CuI (139 mg, 0.73 mmol, 0.1 eq) Et3N (2.2 g, 21.9 mmol, 3.0 eq) and ethynyltrimethylsilane (1.4 g, 14.6 mmol, 1.2 eq) in THF (20 ml) was stirred at 35° C. for 4 h. The mixture was filtered and concentrated. The residue was purified by silica gel column chromatography (PE/EtOAc=200:1) to give compound 2,4-dichloro-5-((trimethylsilyl)ethynyl)pyrimidine (1.0 g, 56%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography (PE/EtOAc=200:1)

Sources & evidence

ORD record
ord-5e0f7018dec64148b90a8e0bf8b6f567
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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