Hydrochloric Acid → HCID 86642172, compound

HRID 1474751Notes

Reaction equation

HRID 1474751 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[C@H:18]3[C@H:14]([O:15]C(C)(C)[O:17]3)[CH2:13][S:12]2)=[C:4]([Cl:21])[N:3]=1.Cl.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[C@@H:18]([OH:17])[C@H:14]([OH:15])[CH2:13][S:12]2)=[C:4]([Cl:21])[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 16735277HCID 16735277, compound

Product 1

HCID 86642172HCID 86642172, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-dichloro-9-((3aR,4R,6aS)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)-9H-purine, prepared in Step 1, in tetrahydrofuran (20 ml) was added 2 N HCl, followed by stirring the solution overnight. The reaction mixture was neutralized with 1 N sodium hydroxide and carefully concentrated in a vacuum. The concentrate was purified through silica gel column chromatography using a mixture of dichloromethane:methanol (20:1, v/v) as an elution solvent to afford the object compound as a white solid (1.94 g, 96%).

Workup

  1. concentrationcarefully concentrated in a vacuum
  2. customThe concentrate was purified through silica gel column chromatography
  3. additiona mixture of dichloromethane:methanol (20:1

Sources & evidence

ORD record
ord-33ce8c020f95478f886735f2c15b9a29
Source dataset
uspto-grants-2015_04
Patent number
US09018371B2

Reaction notes

Loading…