Tetrabutylammonium Fluoride → HCID 86669454, compound

HRID 2041741Notes

Reaction equation

HRID 2041741 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]#[C:15][Si](C(C)C)(C(C)C)C(C)C)=[CH:11][CH:12]=2)[C@H:7]([NH:26][C:27]2[N:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH2:6][C@@H:5]1[CH3:33])(=[O:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]#[CH:15])=[CH:11][CH:12]=2)[C@H:7]([NH:26][C:27]2[N:28]=[CH:29][CH:30]=[CH:31][N:32]=2)[CH2:6][C@@H:5]1[CH3:33])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67207801HCID 67207801, compound

Product 1

HCID 86669454HCID 86669454, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2S,4R)-1-acetyl-2-methyl-N-2-pyrimidinyl-6-{[tris(1-methylethyl)silyl]ethynyl}-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see Intermediate 113) (220 mg, 0.475 mmol) in tetrahydrofuran (THF) (5 mL) at room temperature was treated with TBAF (1N in THF, 0.571 mL, 0.571 mmol) and the resulting mixture was stirred at this temperature for 30 min then most of the solvent was removed in vacuo. The residue was partitioned between AcOEt and water and the layers were separated. The organic phase was washed with water then brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by SP4 using a 10 G column (gradient:5 to 25% (20% MeOH in DCM) in DCM) gave (2S,4R)-1-acetyl-6-ethynyl-2-methyl-N-2-pyrimidinyl-1,2,3,4-tetrahydro-4-quinolinamine as an orange foam.

Workup

  1. customat room temperature
  2. custommost of the solvent was removed in vacuo
  3. customThe residue was partitioned between AcOEt and water
  4. customthe layers were separated
  5. washThe organic phase was washed with water
  6. dry with materialbrine, dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by SP4

Sources & evidence

ORD record
ord-3262fe030f8a4bbab6395d5f5c0e1de2
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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