Diazabicyclo[5.4.0]undec-7-ene → 8-(((3R,3aR,6R,6aS)-6-((tert-butyldimethyl-silyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)oxy)-2-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-purine

HRID 929190Notes

Reaction equation

HRID 929190 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:7](S(C)(=O)=O)=[N:8]2)=[CH:4][N:3]=1.[Si:23]([O:30][C@H:31]1[C@H:35]2[O:36][CH2:37][C@@H:38]([OH:39])[C@H:34]2[O:33][CH2:32]1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].N12CCCC=C1CCCCN2>CN(C=O)C>[Si:23]([O:30][C@H:31]1[C@H:35]2[O:36][CH2:37][C@@H:38]([O:39][C:7]3[N:6]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:5]4[C:9](=[N:10][C:2]([Cl:1])=[N:3][CH:4]=4)[N:8]=3)[C@H:34]2[O:33][CH2:32]1)([C:26]([CH3:29])([CH3:27])[CH3:28])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 9834010Diazabicyclo[5.4.0]undec-7-eneHCID 67050109(3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-olHCID 900424992-chloro-8-(methylsulfonyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-purine

Product 1

HCID 900415468-(((3R,3aR,6R,6aS)-6-((tert-butyldimethyl-silyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)oxy)-2-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-purine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 2-chloro-8-(methylsulfonyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-purine (182 mgs, 0.50 mmol) and (3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-ol (131.0 mg, 0.50 mmol) in anhydrous DMF (4.1 mL) was added diazabicyclo[5.4.0]undec-7-ene (DBU, 0.11 mL, 0.75 mmol). The reaction was stirred under N2 at RT for 16 h and then evaporated under reduced pressure. Flash chromatography of the resulting residue utilizing a 24 g silica RediSep Rf® Gold column and employing a 0-75% EtOAc/hexane gradient afforded the title compound. LC-MS: calculated for C23H39ClN4O5Si2 542.21 observed m/e: 543.53 (M+H)+ (Rt 1.54/2.0 min)

Workup

  1. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4633565f091c4c998b48b5f882aed270
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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