Tetrabutylammonium Fluoride → (S)-(2,4-Dichlorobenzyl)-[1-(5-ethynylpyrimidin-2-yl)-pyrrolidin-3-yl]-amine

HRID 252139Notes

Reaction equation

HRID 252139 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:44]=[C:43]([Cl:45])[CH:42]=[CH:41][C:21]=1[CH2:22][NH:23][C@H:24]1[CH2:28][CH2:27][N:26]([C:29]2[N:34]=[CH:33][C:32]([C:35]#[C:36][Si](C)(C)C)=[CH:31][N:30]=2)[CH2:25]1>O1CCCC1.O.ClCCl>[Cl:19][C:20]1[CH:44]=[C:43]([Cl:45])[CH:42]=[CH:41][C:21]=1[CH2:22][NH:23][C@H:24]1[CH2:28][CH2:27][N:26]([C:29]2[N:30]=[CH:31][C:32]([C:35]#[CH:36])=[CH:33][N:34]=2)[CH2:25]1

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66854856(S)-(2,4-dichlorobenzyl)-[1-(5-trimethylsilanylethynylpyrimidin-2-yl)-pyrrolidin-3-yl]-amine

Product 1

HCID 59860376(S)-(2,4-Dichlorobenzyl)-[1-(5-ethynylpyrimidin-2-yl)-pyrrolidin-3-yl]-amineYield 72%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add tetrabutylammonium fluoride (1.0 mL, 1.0 mmol, 1.0 M solution in tetrahydrofuran) to a stirred solution of (S)-(2,4-dichlorobenzyl)-[1-(5-trimethylsilanylethynylpyrimidin-2-yl)-pyrrolidin-3-yl]-amine (327 mg, 0.78 mmol) in tetrahydrofuran (10 mL) at 0° C. Warm to room temperature and stir for 1 hour and concentrate to give a residue. Dilute the residue with water (10 mL), extract with ethyl acetate (3×25 mL). Extract the combined organic layers with saturated aqueous sodium chloride (10 mL), concentrate to give a residue. Dissolve the residue in dichloromethane, filter, concentrate to give a residue, and chromatograph the residue on silica gel followed by chromatography on SCX-2 to give the title compound as a yellow gum (194 mg, 72%).

Workup

  1. concentrationconcentrate
  2. customto give a residue
  3. extractionextract with ethyl acetate (3×25 mL)
  4. extractionExtract the combined organic layers with saturated aqueous sodium chloride (10 mL)
  5. concentrationconcentrate
  6. customto give a residue
  7. filtrationfilter
  8. concentrationconcentrate
  9. customto give a residue, and chromatograph the residue on silica gel

Sources & evidence

ORD record
ord-dd43cda662fa4ba59e2278cbf5289465
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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