Tetrabutylammonium Fluoride → HCID 86720794, compound

HRID 1753718Notes

Reaction equation

HRID 1753718 reaction equation
[CH2:1]([NH:5][C:6]1[N:11]=[C:10]([NH:12][CH2:13][CH:14]([CH3:16])[CH3:15])[N:9]=[C:8]([C:17]#[C:18][Si](C)(C)C)[N:7]=1)[CH:2]([CH3:4])[CH3:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:17]([C:8]1[N:7]=[C:6]([NH:5][CH2:1][CH:2]([CH3:3])[CH3:4])[N:11]=[C:10]([NH:12][CH2:13][CH:14]([CH3:16])[CH3:15])[N:9]=1)#[CH:18]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 71240594HCID 71240594, compound

Product 1

HCID 86720794HCID 86720794, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N2,N4-diisobutyl-6-((trimethyl-silyl)ethynyl)-1,3,5-triazine-2,4-diamine (27, 14.5 mg, 0.045 mmol) was dissolved in THF (1 mL). Tetrabutylammonium fluoride (0.59 mL, 2.04 mmol) was then added and the reaction mixture was left to react at room temperature (30 min). The reaction was monitored by TLC and when complete, the solvent was removed from the reaction mixture by rotary evaporation to give a crude solid that was purified by flash chromatography on silica gel (hexane/ethyl acetate, 2:1) to afford 45 in 12% yield. 6-ethynyl-N2,N2-diisobutyl-1,3,5-triazine-2,4-diamine (28): Rf: 0.14 (hexane/ethylacetate, 2:1). 1H NMR (400 MHz, CDCl3) δ: 0.92-0.94 (d, 12H), 2.15-2.16 (d, 4H), 3.21-3.27 (m, 2H), 5.29 (s, 1H).

Workup

  1. waitthe reaction mixture was left
  2. customto react at room temperature (30 min)
  3. customthe solvent was removed from the reaction mixture by rotary evaporation
  4. customto give a crude solid that
  5. customwas purified by flash chromatography on silica gel (hexane/ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-583777b7b56e4bafb115721f61560579
Source dataset
uspto-grants-2015_10
Patent number
US09167820B2

Reaction notes

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