Triethylamine → 4-Chloro-5-[(4-chlorophenyl)ethynyl]pyrimidine

HRID 1271028Notes

Reaction equation

HRID 1271028 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.[Cl:10][C:11]1[C:16](I)=[CH:15][N:14]=[CH:13][N:12]=1.C(N(CC)CC)C>ClCCl.[Cu](I)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:10][C:11]1[C:16]([C:9]#[C:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:15][N:14]=[CH:13][N:12]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 70118Benzene, 1-chloro-4-ethynyl-HCID 112302044-Chloro-5-iodopyrimidine

Product 1

HCID 184525694-Chloro-5-[(4-chlorophenyl)ethynyl]pyrimidineYield 11%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.6 g of 1-chloro-4-ethynylbenzene, 1.44 g of 4-chloro-5-iodopyrimidine (J. Chem. Soc. Perkins Trans. I, 1977,621, Allen et al), 7.0 cc of triethylamine, 58 mg of copper iodide and 108 mg of dichlorobis(triphenylphosphine)palladium II was stirred at room temperature under nitrogen for 18 hours. The reaction mixture was evaporated in vacuo. The resulting tan solid was partitioned between water and dichloromethane and the organic extracts washed twice with water, dried over sodium sulfate and evaporated to give a dark brown solid, 1.57 g. The solid was redissolved in dichloromethane and hexanes added to give 120 mg of a beige powder after filtration. The filtrate was purified by column chromatography on silica gel using 1:1 ethyl acetate/dichloromethane as the eluant. The middle rf spot fractions (silica gel TLC in 1:1) were pooled and evaporated to give 0.8 g of a yellow solid, 4-chloro-5-(4-chlorophenylethynyl)-pyrimidine

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customThe resulting tan solid was partitioned between water and dichloromethane
  3. washthe organic extracts washed twice with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto give a dark brown solid, 1.57 g

Sources & evidence

ORD record
ord-3dc0220770094928ac9178ae3bb86c0c
Source dataset
uspto-grants-2007_04
Patent number
US07205297B2

Reaction notes

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