Tetrabutylammonium Fluoride → HCID 90403316, compound

HRID 2200552Notes

Reaction equation

HRID 2200552 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([O:11][CH2:12][CH2:13][O:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:25])([F:24])[F:23])[CH:16]=3)[N:7](COCC[Si](C)(C)C)[C:6]=2[C:5](=[O:34])[N:4]([CH2:35][CH2:36][CH2:37][O:38][CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][O:40]2)[C:3]1=[O:45].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([O:11][CH2:12][CH2:13][O:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:24])([F:23])[F:25])[CH:16]=3)[NH:7][C:6]=2[C:5](=[O:34])[N:4]([CH2:35][CH2:36][CH2:37][O:38][CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][O:40]2)[C:3]1=[O:45]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90402773HCID 90402773, compound

Product 1

HCID 90403316HCID 90403316, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-8-(2-(3-(trifluoromethoxy)phenoxy)ethoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione (1.2 g, 1.82 mmol) in THF (15 mL) was added TBAF (3.7 mL, 3.64 mmol). The mixture was stirred at 80° C. overnight. Then it was cooled, partitioned between ethyl acetate and water. The organic layers were combined, washed with water, dried over sodium sulfate, filtered and concentrated to give a crude product which was purified by column chromatography eluting with petroleum ether and ethyl acetate (2:1) to give 3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-8-(2-(3-(trifluoromethoxy)phenoxy)ethoxy)-1H-purine-2,6(3H,7H)-dione (900 mg, 93.7% yield) as a white solid. LCMS retention time 1.613; LCMS MH+-THP 445.

Workup

  1. temperatureThen it was cooled
  2. custompartitioned between ethyl acetate and water
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product which
  8. customwas purified by column chromatography
  9. washeluting with petroleum ether and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-bf715fbfa97747d4a7a4c82e5e6bf4f9
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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