p-Toluenesulfonic acid → HCID 178521062, compound

HRID 641152Notes

Reaction equation

HRID 641152 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@H:7]([OH:8])[C@H:6]([OH:9])[C@H:5]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH:19][CH:20]2[CH2:24][CH2:23][O:22][CH2:21]2)[O:4]1.COC(OC)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C=O.CO>[CH2-:2][C:3]([CH3:7])=[O:4].[OH:1][CH2:2][C@@H:3]1[C@H:7]([OH:8])[C@H:6]([OH:9])[C@H:5]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH:19][CH:20]2[CH2:24][CH2:23][O:22][CH2:21]2)[O:4]1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 66696639HCID 66696639, compound

Product 1

HCID 178521062HCID 178521062, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (4S,2R,3R,5R)-2-hydroxymethyl-5-[6-(tetrahydrofuran-3-ylamino)-purin-9-yl]-tetrahydrofuran-3,4-diol, a compound of formula (2), (2.0 g, 6.0 mmol) and 2,2-dimethoxypropane (1.2 g, 11.8 mmol) in dimethylformamide (20 mL) was added p-toluenesulfonic acid (50 mg, 0.26 mmol) at 70° C. After 48 hours at 70° C., the reaction was concentrated in vacuum to afford a solid. The solid was dissolved in methanol (3 mL), then triturated with ethyl ether (50 mL), to afford (4S,2R,3R,5R)-2-hydroxymethyl-5-[6-(tetrahydrofuran-3-ylamino)-purin-9-yl]-tetrahydrofuran-3,4-diol acetonide.

Workup

  1. concentrationthe reaction was concentrated in vacuum
  2. customto afford a solid
  3. customtriturated with ethyl ether (50 mL)

Sources & evidence

ORD record
ord-4d2629d489bf483f91959652ffcd9d5c
Source dataset
uspto-grants-2010_04
Patent number
US07696181B2

Reaction notes

Loading…