Hexamethyldisilazane → (2R,3R,4R,5R)-4-(Benzoyloxy)-5-[2-cyano-6-(phenethylamino)-9H-purin-9-yl]-2-(methoxymethyl)tetrahydro-3-furanyl benzoate

HRID 2268431Notes

Reaction equation

HRID 2268431 reaction equation
[CH2:1]([NH:9][C:10]1[N:18]=[C:17]([C:19]#[N:20])[N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][NH:14]2)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:21]([O:29][C@H:30]1[C@@H:34]([O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@H:33](OC(=O)C)[O:32][C@@H:31]1[CH2:48][O:49][CH3:50])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O[C@H]1[C@@H](OC(=O)C2C=CC=CC=2)[C@@H](OC(=O)C)O[C@@H]1COC)(=O)C1C=CC=CC=1.S([O-])([O-])(=O)=O.[NH4+].[NH4+].C[Si](C)(C)N[Si](C)(C)C.Br[Si](C)(C)C>[Bi](Br)(Br)Br.ClCCl.C(#N)C>[C:21]([O:29][C@H:30]1[C@@H:34]([O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@H:33]([N:14]2[CH:13]=[N:12][C:11]3[C:15]2=[N:16][C:17]([C:19]#[N:20])=[N:18][C:10]=3[NH:9][CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[O:32][C@@H:31]1[CH2:48][O:49][CH3:50])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

10

Reactant 6

HCID 13838HexamethyldisilazaneHCID 76113BromotrimethylsilaneHCID 6097028Ammonium SulfateHCID 69534087(2R,3R,4R,5R)-5-(acetyloxy)-4-(benzoyloxy)-2-(methoxymethyl)tetrahydro-3-furanyl benzoateHCID 69534095(2R,3R,4R,5S)-5-(acetyloxy)-4-(benzoyloxy)-2-(methoxymethyl)tetrahydro-3-furanyl benzoateHCID 178510600HCID 178510600, compound

Product 1

HCID 59975283(2R,3R,4R,5R)-4-(Benzoyloxy)-5-[2-cyano-6-(phenethylamino)-9H-purin-9-yl]-2-(methoxymethyl)tetrahydro-3-furanyl benzoate

Reagents, catalysts & solvents 3

HCID 82232bismuth(III) bromideCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by a similar method to preparation 11 using 6-(phenethylamino)-9H-purine-2-carbonitrile (3.8 g, 11.2 mmol) (preparation 45), (2R,3R,4R,5S)-5-(acetyloxy)-4-(benzoyloxy)-2-(methoxymethyl)tetrahydro-3-furanyl benzoate and (2R,3R,4R,5R)-5-(acetyloxy)-4-(benzoyloxy)-2-(methoxymethyl)tetrahydro-3-furanyl benzoate (preparation 4) (6 g, 14.5 mmol), ammonium sulfate (200 mg, 1.2 mmol), 1,1,1,3,3,3-hexamethyidisilazane (150 ml), bromotrimethylsilane (8 ml, 177 mmol), acetonitrile (80 ml), dichloromethane (80 ml) and bismuth tribromide (0.35 g, 0.24 mmol). The product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (99.5:0.5). This gave the title compound (7.9 g) as a white foam. MS: 619 (MH+).

Workup

  1. customThe product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (99.5:0.5)

Sources & evidence

ORD record
ord-d0161171eeee41c795f891434c6eb1cc
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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