Triethylamine → 5-Methyl-6-((trimethylsilyl)ethynyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

HRID 657697Notes

Reaction equation

HRID 657697 reaction equation
I[C:2]1[C:3]([CH3:12])=[N:4][C:5]2[N:6]([N:9]=[CH:10][N:11]=2)[C:7]=1[NH2:8].[C:13]([Si:15]([CH3:18])([CH3:17])[CH3:16])#[CH:14].C(N(CC)CC)C>C(#N)C.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>[CH3:12][C:3]1[C:2]([C:14]#[C:13][Si:15]([CH3:18])([CH3:17])[CH3:16])=[C:7]([NH2:8])[N:6]2[N:9]=[CH:10][N:11]=[C:5]2[N:4]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 667428896-Iodo-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

Product 1

HCID 667431075-Methyl-6-((trimethylsilyl)ethynyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amineYield 50.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of Example 4A (275 mg, 1.0 mmol), ethynyltrimethylsilane (283 μL, 2.6 mmol), bis(triphenylphosphine)palladium(II) dichloride (35 mg, 0.05 mmol), CuI (10 mg, 0.05 mmol), and triethylamine (279 μL, 2 mmol) in acetonitrile (4 mL) was heated at 90° C. under an atmosphere of nitrogen for 1 h. The resulting-mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4), filtered, and concentrated in vacuuo. The residue was purified by flash chromatograph on silica gel (eluting with ethyl acetate) to provide the title compound as a pale yellow solid (123 mg, 50% yield).

Workup

  1. customThe resulting-mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuuo
  6. customThe residue was purified by flash chromatograph on silica gel (eluting with ethyl acetate)

Sources & evidence

ORD record
ord-b4d173e0ad9c4ac99ad1dd7fad851c93
Source dataset
uspto-grants-2011_12
Patent number
US08076344B2

Reaction notes

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