2-{6-[(Trimethylsilyl)ethynyl]pyridin-2-yl}pyrimidine → 2-(6-Ethynylpyridin-2-yl)pyrimidine

HRID 705032Notes

Reaction equation

HRID 705032 reaction equation
C[Si]([C:5]#[C:6][C:7]1[N:12]=[C:11]([C:13]2[N:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:10]=[CH:9][CH:8]=1)(C)C>O1CCCC1>[C:6]([C:7]1[N:12]=[C:11]([C:13]2[N:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:10]=[CH:9][CH:8]=1)#[CH:5]

Participants

3

Reactant 1

HCID 675133982-{6-[(Trimethylsilyl)ethynyl]pyridin-2-yl}pyrimidine

Product 1

HCID 866981402-(6-Ethynylpyridin-2-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon, 500 mg (1.97 mmol) of 2-{6-[(trimethylsilyl)ethynyl]pyridin-2-yl}pyrimidine were initially charged in 20 ml of tetrahydrofuran at −5° C., 2.37 ml (2.37 mmol) of a 1 M solution of N,N,N-tributylbutane-1-ammonium fluoride in tetrahydrofuran were added and the mixture was stirred at this temperature for 2 hours. For work-up, the reaction mixture was filtered through silica gel (ethyl acetate), concentrated under reduced pressure and purified chromatographically. This gave 311 mg (87% of theory) of 2-(6-ethynylpyridin-2-yl)pyrimidine.

Workup

  1. filtrationFor work-up, the reaction mixture was filtered through silica gel (ethyl acetate)
  2. concentrationconcentrated under reduced pressure
  3. custompurified chromatographically

Sources & evidence

ORD record
ord-eeab3f85173c43e9801d613636d9cdc4
Source dataset
uspto-grants-2015_11
Patent number
US09173396B2

Reaction notes

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