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

HRID 2268350Notes

Reaction equation

HRID 2268350 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[C@H:13]2[C@H:17]([O:18][Si](C(C)(C)C)(C)C)[C@H:16]([O:26][Si](C(C)(C)C)(C)C)[C@@H:15]([CH2:34][O:35][CH3:36])[O:14]2)=[C:6]([NH:37][CH2:38][CH:39]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:5]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[NH2:1][CH2:2][CH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[C@H:13]2[C@H:17]([OH:18])[C@H:16]([OH:26])[C@@H:15]([CH2:34][O:35][CH3:36])[O:14]2)=[C:6]([NH:37][CH2:38][CH:39]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[N:5]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69534061N-{2-(2-Aminoethyl)-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-9H-purin-6-yl}-N-(2,2-diphenylethyl)amine

Product 1

HCID 9957801(2R,3R,4S,5R)-2-{2-(2-Aminoethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiolYield 103.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-{2-(2-Aminoethyl)-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-9H-purin-6-yl}-N-(2,2-diphenylethyl)amine (1.07 g, 1.46 mmol) (preparation 18) was dissolved in dry tetrahydrofuran (4 ml), a 1M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (6 ml, 6 mmol) added and the mixture stirred at room temperature for 2.5 hr. The solvent was removed under reduced pressure and the residue dissolved in dichloromethane. The solvent was again removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (90:10:1), to give the product as a foam (760 mg). MS: 505 (MH+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane
  3. customThe solvent was again removed under reduced pressure
  4. customthe residue purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (90:10:1)

Sources & evidence

ORD record
ord-c45bc8cfff1a410193ac5d6d7121f007
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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