Triethylamine → 2-Methoxy-5-((trimethylsilyl)ethynyl)pyrimidine

HRID 1958754Notes

Reaction equation

HRID 1958754 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH3:10][Si:11]([CH2:14][CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C>C(OCC)(=O)C.O.[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>[CH3:9][O:8][C:5]1[N:4]=[CH:3][C:2]([C:15]#[C:14][Si:11]([CH3:13])([CH3:12])[CH3:10])=[CH:7][N:6]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 137936EthyltrimethylsilaneHCID 139657Pyrimidine, 5-bromo-2-methoxy-

Product 1

HCID 687422722-Methoxy-5-((trimethylsilyl)ethynyl)pyrimidineYield 98.2%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 5-bromo-2-methoxypyrimidine (500 mg, 2.7 mmol) in ethyl acetate (2 mL) and water (0.2 mL) was added trimethylsilylethane (0.41 mL, 3 mmol), triethylamine (0.75 mL, 5.4 mmol), copper iodide (25 mg, 0.13 mmol) and bis(triphenylphosphine)palladium(II) dichloride (47 mg, 0.067 mmol). The solution was heated to 60° C. for 16 h. Ethyl acetate (100 mL) was added and the solution was washed with water (3×10 mL), dried over MgSO4 and treated with decolorizing charcoal. Ethyl acetate was removed in vacuo to give the title compound as a clear oil (547 mg, 97%). 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 2H), 4.01 (s, 3H), 0.24 (s, 9H).

Workup

  1. washthe solution was washed with water (3×10 mL)
  2. dry with materialdried over MgSO4
  3. additiontreated with decolorizing charcoal
  4. customEthyl acetate was removed in vacuo

Sources & evidence

ORD record
ord-d12bb0f6e77d481898d35bb13a2dc50d
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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