N-Cyclobutyl-6-(2-(trimethylsilyl)ethynyl)pyridazin-3-amine → N-Cyclobutyl-6-ethynylpyridazin-3-amine

HRID 535811Notes

Reaction equation

HRID 535811 reaction equation
[CH:1]1([NH:5][C:6]2[N:7]=[N:8][C:9]([C:12]#[C:13][Si](C)(C)C)=[CH:10][CH:11]=2)[CH2:4][CH2:3][CH2:2]1>C(Cl)Cl.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[CH:1]1([NH:5][C:6]2[N:7]=[N:8][C:9]([C:12]#[CH:13])=[CH:10][CH:11]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 86709553N-Cyclobutyl-6-(2-(trimethylsilyl)ethynyl)pyridazin-3-amine

Product 1

HCID 86709554N-Cyclobutyl-6-ethynylpyridazin-3-amineYield 75.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

Into a solution of N-cyclobutyl-6-(2-(trimethylsilyl)ethynyl)pyridazin-3-amine (0.49 g, 2 mmol) in CH2Cl2, TBAF was added. The reaction was monitored by TLC. The reaction mixture was concentrated and the residue obtained was purified by silica gel chromatography (eluent: 30% ethyl acetate in n-hexane, ethyl acetate was added 0.5% Et3N) to give an off-white solid (0.26 g, 75.1%). 1H NMR (300 MHz, CDCl3) δ: 7.26-7.29 (1H, d, J=9.0 Hz), 6.51-6.54 (1H, d, J=9.0 Hz), 5.57 (1H, s), 4.17-4.24 (1H, m), 3.21 (1H, s), 2.40-2.46 (2H, m), 1.89-1.98 (2H, m), 1.77-1.85 (2H, m).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue obtained
  3. customwas purified by silica gel chromatography (eluent: 30% ethyl acetate in n-hexane, ethyl acetate was added 0.5% Et3N)

Sources & evidence

ORD record
ord-02f1d32ad41d46e4aca97d7efb827010
Source dataset
uspto-grants-2014_10
Patent number
US08859553B2

Reaction notes

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