Potassium Carbonate → 5-Amino-3-((2R,3R,5S)-3-azido-5-((S)-1-hydroxyethyl)tetrahydrofuran-2-yl)thiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione

HRID 60728Notes

Reaction equation

HRID 60728 reaction equation
C([O:9][CH:10]([C@@H:12]1[CH2:16][C@@H:15]([N:17]=[N+:18]=[N-:19])[C@H:14]([N:20]2[C:24]3[N:25]=[C:26]([NH2:30])[NH:27][C:28](=[O:29])[C:23]=3[S:22][C:21]2=[O:31])[O:13]1)[CH3:11])(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CO>[NH2:30][C:26]1[NH:27][C:28](=[O:29])[C:23]2[S:22][C:21](=[O:31])[N:20]([C@H:14]3[C@H:15]([N:17]=[N+:18]=[N-:19])[CH2:16][C@@H:12]([C@@H:10]([OH:9])[CH3:11])[O:13]3)[C:24]=2[N:25]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 1371087471-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-azido-tetrahydrofuran-2-yl]ethyl benzoate2×

Product 1

HCID 1371086945-Amino-3-((2R,3R,5S)-3-azido-5-((S)-1-hydroxyethyl)tetrahydrofuran-2-yl)thiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dioneYield 6.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-azido-tetrahydrofuran-2-yl]ethyl benzoate (compound 25l, 600 mg, crude) in MeOH (8 mL) was added K2CO3 (187 mg, 1.4 mmol). After being stirred at room temperature for 5 hours, the reaction mixture was concentrated in vacuo and the residue was purified by preparative HPLC to afford 30 mg of 5-amino-3-[(2R,3R,5S)-3-azido-5-(1-hydroxyethyl)tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione (Example 25) as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-7ff0a91c9b2240b3a12fe5592499b929
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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