Tetrabutylammonium Fluoride → 4-(6-Ethynyl-2-methyl-1,3-benzodiazol-1-yl)-1,3,5-triazin-2-amine

HRID 1398700Notes

Reaction equation

HRID 1398700 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH2:13])[N:8]=2)[C:5]2[CH:14]=[C:15]([C:18]#[C:19][Si](C)(C)C)[CH:16]=[CH:17][C:4]=2[N:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:18]([C:15]1[CH:16]=[CH:17][C:4]2[N:3]=[C:2]([CH3:1])[N:6]([C:7]3[N:12]=[CH:11][N:10]=[C:9]([NH2:13])[N:8]=3)[C:5]=2[CH:14]=1)#[CH:19]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 681816854-{2-Methyl-6-[2-(trimethylsilyl)ethynyl]-1,3-benzodiazol-1-yl}-1,3,5-triazin-2-amine

Product 1

HCID 866696174-(6-Ethynyl-2-methyl-1,3-benzodiazol-1-yl)-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-{2-methyl-6-[2-(trimethylsilyl)ethynyl]-1,3-benzodiazol-1-yl}-1,3,5-triazin-2-amine (90 mg, 0.279 mmol) in THF (1 mL) was added 1M TBAF in THF (0.33 mL, 0.33 mmol). The mixture was allowed to stand at RT for 1 hr, the mixture was concentrated in vacuo and purified by column chromatography (Biotage 5-8% MeOH/DCM) to give the title compound; LC-MS: m/z+250.95 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. custompurified by column chromatography (Biotage 5-8% MeOH/DCM)

Sources & evidence

ORD record
ord-85f2581f28b448d5978650c5b358b131
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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