Tetrabutylammonium Fluoride → (2R,3R,4S,5R)-2-{2-[(Benzyloxy)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268370Notes

Reaction equation

HRID 2268370 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[C@H:19]2[C@H:23]([O:24][Si](C(C)(C)C)(C)C)[C@H:22]([O:32][Si](C(C)(C)C)(C)C)[C@@H:21]([CH2:40][O:41][CH3:42])[O:20]2)=[C:12]([NH:43][CH2:44][CH:45]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:8][CH2:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[C@H:19]2[C@H:23]([OH:24])[C@H:22]([OH:32])[C@@H:21]([CH2:40][O:41][CH3:42])[O:20]2)=[C:12]([NH:43][CH2:44][CH:45]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[N:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 695340912-[(Benzyloxy)methyl]-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-N-(2,2-diphenylethyl)-9H-purin-6-amine

Product 1

HCID 9851252(2R,3R,4S,5R)-2-{2-[(Benzyloxy)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiolYield 53.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-[(Benzyloxy)methyl]-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-N-(2,2-diphenylethyl)-9H-purin-6-amine (65 mg, 0.08 mmol) (preparation 24) was dissolved in stirred tetrahydrofuran (10 ml) and a 1 molar solution of tetra-n-butylammonium fluoride in tetrahydrofuran (0.5 ml, 0.5 mmol) added. The reaction mixture was stirred at room temperature for 15 min. The solvent was removed under reduced pressure and the residue partitioned between saturated aqueous sodium hydrogen carbonate solution and ethyl acetate. The ethyl acetate layer was separated, washed with brine and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a residue which was purified by column chromatography on silica gel eluting with a solvent system of ethyl acetate:hexane (3:1) increasing in polarity to ethyl acetate:methanol (97:3). This gave the title compound (25 mg) as a gum. MS: 604 (MNa+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between saturated aqueous sodium hydrogen carbonate solution and ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. washwashed with brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customto give a residue which
  8. customwas purified by column chromatography on silica gel eluting with a solvent system of ethyl acetate:hexane (3:1)
  9. temperatureincreasing in polarity to ethyl acetate:methanol (97:3)

Sources & evidence

ORD record
ord-75731e54210441958a8c4ed79319fe64
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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