Sodium Methoxide → 9-[(3aR,4R,6R,6aR)-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-(2-methoxyethyl)-9H-purine

HRID 552768Notes

Reaction equation

[Si:1]([O:8][CH2:9][C@@H:10]1[C@H:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@H:13]2[C@H:12]([N:20]2[CH:28]=[N:27][C:26]3[C:21]2=[N:22][CH:23]=[N:24][C:25]=3[CH:29]=[CH2:30])[O:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:31][O-:32].[Na+]>C(Cl)Cl>[Si:1]([O:8][CH2:9][C@@H:10]1[C@H:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@H:13]2[C@H:12]([N:20]2[CH:28]=[N:27][C:26]3[C:21]2=[N:22][CH:23]=[N:24][C:25]=3[CH2:29][CH2:30][O:32][CH3:31])[O:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 9-[(3aR,4R,6R,6aR)-6-({[tert-butyl(dimethyl)silyl]oxy}-methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-vinyl-9H-purine (100 mg, 0.23 mmol) in DCM (5.0 mL) was added NaOMe (0.5M in MeOH, 4.6 mL, 2.2 mmol) at 0° C. The reaction was stirred for 2 h at 0° C. and r.t. overnight. The mixture was diluted with DCM and washed with saturated aq NH4Cl. The organic layer was dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (0 to 10% MeOH/DCM) to yield 70 mg (66%) of the title compound.

Workup

washwashed with saturated aq NH4Cl
dry with materialThe organic layer was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash chromatography (0 to 10% MeOH/DCM)

Sources & evidence

ORD record: ord-94429a648bd4415688d4c0fa778f5530
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951810B2

Reaction notes

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