Tetrabutylammonium Fluoride → 7-Ethynyl-4-(methylthio)thieno[3,2-d]pyrimidine

HRID 1465034Notes

Reaction equation

HRID 1465034 reaction equation
[CH3:1][S:2][C:3]1[C:4]2[S:11][CH:10]=[C:9]([C:12]#[C:13][Si](C)(C)C)[C:5]=2[N:6]=[CH:7][N:8]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:12]([C:9]1[C:5]2[N:6]=[CH:7][N:8]=[C:3]([S:2][CH3:1])[C:4]=2[S:11][CH:10]=1)#[CH:13]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 673274394-(Methylthio)-7-((trimethylsilyl)ethynyl)thieno[3,2-d]pyrimidine

Product 1

HCID 866741357-Ethynyl-4-(methylthio)thieno[3,2-d]pyrimidineYield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(Methylthio)-7-((trimethylsilyl)ethynyl)thieno[3,2-d]pyrimidine (500 mg, 1.8 mmol) was dissolved in THF (5 mL) at 1.0M and then tetrabutylammonium fluoride solution (3.6 mL, 3.6 mmol) was added thereto. The reaction mixture was stirred at room temperature for 30 minutes and then concentrated. The resulting mixture was purified by silica gel chromatography (ethyl acetate/hexane=2:8˜3:7) to obtain the title compound (340 mg, 91% yield) as a yellowish solid.

Workup

  1. concentrationconcentrated
  2. customThe resulting mixture was purified by silica gel chromatography (ethyl acetate/hexane=2:8˜3:7)

Sources & evidence

ORD record
ord-031fd6c366114e0e8991eb1c4ecf63f0
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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