Hydrochloric Acid → HCID 67164151, compound

HRID 552698Notes

Reaction equation

[C@@H:1]1([NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][N:15]3[C@@H:20]2O[C@H]3[C@@H:22]([O:23][Si:24]([CH:40]([CH3:42])[CH3:41])([CH:37]([CH3:39])[CH3:38])[O:25][Si:26]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[O:27]C3)[C@@H:21]2[O:43][CH3:44])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl.[CH3:46][OH:47].[O:48]1CCOC[CH2:49]1>>[C@@H:1]1([NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][N:15]3[C@@H:20]2[O:47][C@H:46]([CH2:49][OH:48])[C@@H:22]([O:23][Si:24]([CH:40]([CH3:42])[CH3:41])([CH:37]([CH3:39])[CH3:38])[O:25][Si:26]([CH:31]([CH3:33])[CH3:32])([CH:34]([CH3:35])[CH3:36])[OH:27])[C@@H:21]2[O:43][CH3:44])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 21966525Dioxane Methanol

HCID 67163894HCID 67163894, compound

Product 1

HCID 67164151HCID 67164151, compoundYield 13%

Procedure

To a solution of N-[(1S)-2,3-dihydro-1H-inden-1-yl]-9-[(6aR,8R,9S,9aR)-2,2,4,4-tetraisopropyl-9-methoxytetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-9H-purin-6-amine (238 mg, 0.37 mmol) in methanol/dioxane (1:4, 8 mL) was added 3.2 mL 0.2N HCl. After stirring for two hours the solvent was removed in vacuo and the residue purified by silica gel chromatography (10 to 50% EtOAc/hexanes) to afford 32 mg (13%) of the title compound.

Workup

customwas removed in vacuo
customthe residue purified by silica gel chromatography (10 to 50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-a7370512b75342ceb93bf8c5410cf560
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951810B2

Reaction notes

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