Acetic Acid → 5-amino-3-[(2R,3R,5S)-5-[cyclopentyl(hydroxy)methyl]-3-hydroxy-tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione

HRID 60707Notes

Reaction equation

HRID 60707 reaction equation
C([O:9][CH:10]([C@@H:16]1[CH2:20][C@@H:19]([O:21]C(=O)C)[C@H:18]([N:25]2[C:29]3[N:30]=[C:31]([NH2:35])[NH:32][C:33](=[O:34])[C:28]=3[S:27][C:26]2=[O:36])[O:17]1)[CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CC(O)=O>CO>[NH2:35][C:31]1[NH:32][C:33](=[O:34])[C:28]2[S:27][C:26](=[O:36])[N:25]([C@H:18]3[C@H:19]([OH:21])[CH2:20][C@@H:16]([CH:10]([CH:11]4[CH2:15][CH2:14][CH2:13][CH2:12]4)[OH:9])[O:17]3)[C:29]=2[N:30]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 137108746[[(2S,4R,5R)-4-acetoxy-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-2-yl]-cyclopentyl-methyl] benzoate2×

Product 1

HCID 1371087075-amino-3-[(2R,3R,5S)-5-[cyclopentyl(hydroxy)methyl]-3-hydroxy-tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dioneYield 9.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [[(2S,4R,5R)-4-acetoxy-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-2-yl]-cyclopentyl-methyl] benzoate (compound 11d, 70 mg, 0.14 mmol) in methanol (10 mL) was added K2CO3 (136 mg, 1 mmol). After being stirred at room temperature for 12 hours, the reaction mixture was adjusted to pH 7.0 by addition of HOAc (120 mg, 2 mmol), concentrated in vacuo and the residue was purified by preparative HPLC to afford 4.7 mg of 5-amino-3-[(2R,3R,5S)-5-[cyclopentyl(hydroxy)methyl]-3-hydroxy-tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione (Example 11) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-429ceaebe0fc404cbaf8d0f9f79da7b1
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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