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

HRID 1965947Notes

Reaction equation

HRID 1965947 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5](I)=[CH:4][N:3]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:36][Si:37]([C:40]#[CH:41])([CH3:39])[CH3:38]>C1COCC1.[Pd](Cl)Cl.[Cu](I)I>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:41]#[C:40][Si:37]([CH3:39])([CH3:38])[CH3:36])=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 2634382,4-Dichloro-5-iodopyrimidine

Product 1

HCID 210809892,4-Dichloro-5-((trimethylsilyl)ethynyl)pyrimidine

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

66.55 g of 2,4-dichloro-5-iodo-pyrimidine is stirred for three hours in 1.2 litres of absolute THF with 70 ml of triethylamine, 4.9 g of palladium chloride, 13.3 g of triphenylphosphine, 4 g of copper iodide and 39.3 ml of trimethylsilylacetylene at 40° C. After the reaction has ended the solvent is eliminated in vacuo and the dark red oil remaining is subjected to fractional distillation. The product is distilled over at 0.01 Torr and 100° C.

Workup

  1. distillationthe dark red oil remaining is subjected to fractional distillation
  2. distillationThe product is distilled over at 0.01 Torr and 100° C.

Sources & evidence

ORD record
ord-00803ae75a2e410ca9c6b75faccb1d8e
Source dataset
uspto-grants-2013_04
Patent number
US08420630B2

Reaction notes

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