Thiophenol → (2R,3R,4S,5R)-2-{6-[(2,2-Diphenylethyl)amino]-2-[(phenylsulfanyl)methyl]-9H-purin-9-yl}-5(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268376Notes

Reaction equation

HRID 2268376 reaction equation
CS(O[CH2:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@H:16]2[C@H:20]([OH:21])[C@H:19]([OH:22])[C@@H:18]([CH2:23][O:24][CH3:25])[O:17]2)=[C:9]([NH:26][CH2:27][CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:8]=1)(=O)=O.C(N(CC)CC)C.[C:48]1([SH:54])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>O1CCCC1>[C:35]1([CH:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:27][NH:26][C:9]2[N:8]=[C:7]([CH2:6][S:54][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[C@H:16]2[C@H:20]([OH:21])[C@H:19]([OH:22])[C@@H:18]([CH2:23][O:24][CH3:25])[O:17]2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 59975278{9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate

Product 1

HCID 9873095(2R,3R,4S,5R)-2-{6-[(2,2-Diphenylethyl)amino]-2-[(phenylsulfanyl)methyl]-9H-purin-9-yl}-5(methoxymethyl)tetrahydro-3,4-furandiolYield 36.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate (400 mg, 0.7 mmol) (Preparation 25), triethylamine (0.2 ml, 1.4 mmol) and thiophenol (100 mg, 0.9 mmol) were dissolved in tetrahydrofuran (3 ml) and the reaction mixture stirred for 24 hr at room temperature. The solvent was then removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol (99:1) increasing in polarity to (95:5). This gave the title compound (150 mg) as a foam. MS: 584 (MH+).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe residue purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol (99:1)
  3. temperatureincreasing in polarity to (95:5)

Sources & evidence

ORD record
ord-1d8e97824ef5413d95095dff6059ed95
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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