Tetrabutylammonium Fluoride → HCID 86618724, compound

HRID 1397576Notes

Reaction equation

HRID 1397576 reaction equation
[Si]([O:8][CH2:9][C@@H:10]1[C@H:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@H:13]2[C@H:12]([N:20]([CH3:28])[C:21]2[CH:26]=[C:25]([Cl:27])[N:24]=[CH:23][N:22]=2)[CH2:11]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:27][C:25]1[N:24]=[CH:23][N:22]=[C:21]([N:20]([CH3:28])[C@H:12]2[C@@H:13]3[O:17][C:16]([CH3:18])([CH3:19])[O:15][C@@H:14]3[C@@H:10]([CH2:9][OH:8])[CH2:11]2)[CH:26]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86618722HCID 86618722, compound

Product 1

HCID 86618724HCID 86618724, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of N-[(3aS,4R,6R,6aR)-6-({[tert-butyl(dimethyl)silyl]oxy}-methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-6-chloro-N-methylpyrimidin-4-amine (400 mg, 0.93 mmol) in THF (10.0 mL) was added 1M solution of tetra-n-butylammonium fluoride in THF (1.00 mL, 1.00 mmol), and the mixture was stirred for 2 h. After quenching by addition of brine (20.0 mL), the resulting mixture was extracted with ethyl acetate (3×40.0 mL). The organic layers were combined, dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified via silica gel column chromatography eluting with a gradient of 40 to 100% ethyl acetate in DCM to afford the title compound (261 mg, 89%) as a colorless oil. LC/MS: Rt=1.24 min, ES+ 314.2 (AA standard).

Workup

  1. customAfter quenching by addition of brine (20.0 mL)
  2. extractionthe resulting mixture was extracted with ethyl acetate (3×40.0 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customThe residue was purified via silica gel column chromatography
  7. washeluting with a gradient of 40 to 100% ethyl acetate in DCM

Sources & evidence

ORD record
ord-d1e8dc9e9fad4a3296b838cdfbae5599
Source dataset
uspto-grants-2014_12
Patent number
US08901136B2

Reaction notes

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