Tetrabutylammonium Fluoride → HCID 11669062, compound

HRID 253024Notes

Reaction equation

HRID 253024 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[S:17][C:16]3[C:15]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[N:14][C:13]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30][SiH2]C(C)(C)C(C)(C)C)[CH:25]=4)=[N:12][C:11]=3[CH:10]=2)[CH2:4][CH2:3]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[S:17][C:16]3[C:15]([N:18]4[CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)=[N:14][C:13]([C:24]4[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=4)=[N:12][C:11]=3[CH:10]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178480811HCID 178480811, compound

Product 1

HCID 11669062HCID 11669062, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-(4-methyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-2-[3-(1,1,2,2-tetramethyl-propylsilanyloxy)-phenyl]-thieno[3,2-d]pyrimidine (6.95 g, 12.89 mmol) in THF (100 mL) cooled to 0° C. was added a 1.0 M solution of tetrabutyl ammonium fluoride in THF (14.2 mL, 1.1 eq.). After 30 minutes the solvent was removed in vacuo and the residue was purified using flash chromatography (silica, 8% methanol in dichloromethane) and then triturated using ethyl acetate/methanol to yield the title compound as a white solid (4.62 g, 85%).

Workup

  1. customAfter 30 minutes the solvent was removed in vacuo
  2. customthe residue was purified
  3. customtriturated

Sources & evidence

ORD record
ord-27481d1978e6498992af982faa1182c0
Source dataset
uspto-grants-2011_01
Patent number
US07872003B2

Reaction notes

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