Tetrabutylammonium Fluoride → N-((6-ethynyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-7-methoxy-1,5-naphthyridin-4-amine

HRID 1511292Notes

Reaction equation

HRID 1511292 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][CH2:14][C:15]3[N:19]4[N:20]=[C:21]([C:24]#[C:25][Si](CC)(CC)CC)[CH:22]=[CH:23][C:18]4=[N:17][N:16]=3)=[CH:8][CH:9]=[N:10]2)=[N:5][CH:4]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C(O)(=O)C>[C:24]([C:21]1[CH:22]=[CH:23][C:18]2[N:19]([C:15]([CH2:14][NH:13][C:7]3[C:6]4[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][N:5]=4)[N:10]=[CH:9][CH:8]=3)=[N:16][N:17]=2)[N:20]=1)#[CH:25]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 576909307-methoxy-N-((6-(2-(triethylsilyl)ethynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-1,5-naphthyridin-4-amine

Product 1

HCID 57691226N-((6-ethynyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-7-methoxy-1,5-naphthyridin-4-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 7-methoxy-N-((6-(2-(triethylsilyl)ethynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-1,5-naphthyridin-4-amine (0.360 g, 0.808 mmol) in acetic acid (8 mL) was added TBAF (1.21 ml, 1.21 mmol). The mixture was stirred at room temperature overnight, additional TBAF (1.21 ml, 1.21 mmol) was added and the mixture was heated to 50° C. for five hours. The mixture was concentrated and purified via MPLC (eluted with 0-10% (1:10:90 NH4OH:MeOH:DCM) in dichloromethane) to yield the product as an off-white solid. MS m/z=332.0 [M+1]+. Calc'd for C17H13N7O: 331.1.

Workup

  1. temperaturethe mixture was heated to 50° C. for five hours
  2. concentrationThe mixture was concentrated
  3. custompurified via MPLC (eluted with 0-10% (1:10:90 NH4OH:MeOH:DCM) in dichloromethane)

Sources & evidence

ORD record
ord-6c5d12841b574c5faf61c458fd427516
Source dataset
uspto-grants-2012_07
Patent number
US08212041B2

Reaction notes

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