Tetrabutylammonium Fluoride → 4-(2-ethoxy-6-ethynyl-1H-1,3-benzodiazol-1-yl)pyrimidin-2-amine

HRID 1398646Notes

Reaction equation

HRID 1398646 reaction equation
[CH2:1]([O:3][C:4]1[N:8]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[N:10]=2)[C:7]2[CH:16]=[C:17]([C:20]#[C:21][Si](C)(C)C)[CH:18]=[CH:19][C:6]=2[N:5]=1)[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([O:3][C:4]1[N:8]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[N:10]=2)[C:7]2[CH:16]=[C:17]([C:20]#[CH:21])[CH:18]=[CH:19][C:6]=2[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 681816194-{2-ethoxy-6-[2-(trimethylsilyl)ethynyl]-1H-1,3-benzodiazol-1-yl}pyrimidin-2-amine

Product 1

HCID 866696064-(2-ethoxy-6-ethynyl-1H-1,3-benzodiazol-1-yl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-{2-ethoxy-6-[2-(trimethylsilyl)ethynyl]-1H-1,3-benzodiazol-1-yl}pyrimidin-2-amine (170 mg, 0.48 mmol) in dry THF (5 mL) at RT was introduced TBAF (0.58 mL of a 1M solution in THF, 0.58 mmol). After 20 minutes, the reaction mixture was concentrated in vacuo, DCM (5 mL) added, and the solution re-evaporated to dryness in vacuo (re-evaporation process repeated twice). Purification of the residue by column chromatography (Biotage, DCM containing a 1-7% gradient of methanol) furnished the title compound as a beige solid: 1H NMR (500 MHz, DMSO) delta 1.46 (3H, t, J=7.01 Hz), 4.10 (1H, s), 4.61-4.68 (2H, m), 6.97-7.03 (1H, m), 7.09 (2H, br. s.), 7.33 (1H, dd, J=8.12, 1.34 Hz), 7.45 (1H, d, J=8.04 Hz), 8.33 (1H, s), 8.37 (1H, d, J=5.52 Hz); LC-MS: m/z=+280.00 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo, DCM (5 mL)
  2. additionadded
  3. customthe solution re-evaporated to dryness in vacuo (
  4. customre-evaporation process
  5. customPurification of the residue by column chromatography (Biotage, DCM containing a 1-7% gradient of methanol)

Sources & evidence

ORD record
ord-8cf33d0de8ae4638b30ee46dea782f0a
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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