Trimethylsilylacetylene → HCID 66849042, compound

HRID 1992329Notes

Reaction equation

HRID 1992329 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([CH3:8])=[N:6][CH:7]=1.[CH3:9][Si:10]([C:13]#[CH:14])([CH3:12])[CH3:11]>CCN(CC)CC.C1COCC1.[Cu]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>[CH3:8][C:5]1[N:4]=[CH:3][C:2]([C:14]#[C:13][Si:10]([CH3:12])([CH3:11])[CH3:9])=[CH:7][N:6]=1

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 143877445-Bromo-2-methylpyrimidine

Product 1

HCID 66849042HCID 66849042, compoundYield 72.5%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

5-Bromo-2-methyl-pyrimidine (prepared according to UK patent application GB 2 157 288) (0.2 g, 1.16 mmol), (trimethylsilyl)acetylene (164 μL, 1.3 mmol), CuI (0.022 g, 0.116 mmol) and PdCl2(PPh3)2 (0.082 g, 0.116 mmol) in Et3N (2 mL) and THF (2 mL) were stirred at 80° C. for 4 h. After cooling, the solvents were removed under vacuum and the residue chromatographed to give the subtitle compound (0.16 g, 50%).

Workup

  1. temperatureAfter cooling
  2. customthe solvents were removed under vacuum
  3. customthe residue chromatographed

Sources & evidence

ORD record
ord-2d1ac28195a04daf8e1abe61b4d0bf52
Source dataset
uspto-grants-2010_01
Patent number
US07648992B2

Reaction notes

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