Benzyl Bromide → 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

HRID 2268415Notes

Reaction equation

HRID 2268415 reaction equation
[H-].[Na+].[Si:3]([O:10][C@@H:11]1[C@H:15]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[C@@H:14]([CH2:24][O:25][CH3:26])[O:13][C@H:12]1[N:27]1[CH:35]=[N:34][C:33]2[C:28]1=[N:29][C:30]([CH2:51][OH:52])=[N:31][C:32]=2[NH:36][CH2:37][CH:38]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH2:53](Br)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>O1CCCC1>[CH2:53]([O:52][CH2:51][C:30]1[N:29]=[C:28]2[C:33]([N:34]=[CH:35][N:27]2[C@H:12]2[C@H:11]([O:10][Si:3]([C:6]([CH3:8])([CH3:9])[CH3:7])([CH3:4])[CH3:5])[C@H:15]([O:16][Si:17]([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:19])[CH3:18])[C@@H:14]([CH2:24][O:25][CH3:26])[O:13]2)=[C:32]([NH:36][CH2:37][CH:38]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[N:31]=1)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 69534107{9-[(2R,3R,4R,5R)-3,4-Bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methanol

Product 1

HCID 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-amineYield 10.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (23 mg of an 80% dispersion in mineral oil, 0.76 mmol) was added to a stirred solution of {9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methanol (550 mg, 0.76 mmol) (preparation 15) in tetrahydrofuran (3 ml). The reaction mixture was stirred at room temperature for 10 min and then benzyl bromide (0.117 ml, 1 mmol) added. The reaction mixture was stirred for a further 24 hr and then the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of hexane:ethyl acetate (3:1) rising in polarity to (2:1) to give the title compound (65 mg) as a gum. MS: 832 (MNa+).

Workup

  1. stirringThe reaction mixture was stirred for a further 24 hr
  2. customthe solvent removed under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of hexane:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-6110ad57ce154df8b7f9a9938cf807fd
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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