Potassium Carbonate → 5-amino-3-[(2R,3R,5S)-5-(hydroxymethyl)-3-pyrrolidin-1-yloxolan-2-yl]-6H-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione

HRID 60751Notes

Reaction equation

HRID 60751 reaction equation
C([O:9][CH2:10][C@@H:11]1[CH2:15][C@@H:14]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C@H:13]([N:21]2[C:25]3[N:26]=[C:27]([NH2:31])[NH:28][C:29](=[O:30])[C:24]=3[S:23][C:22]2=[O:32])[O:12]1)(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CO>[NH2:31][C:27]1[NH:28][C:29](=[O:30])[C:24]2[S:23][C:22](=[O:32])[N:21]([C@H:13]3[C@H:14]([N:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)[CH2:15][C@@H:11]([CH2:10][OH:9])[O:12]3)[C:25]=2[N:26]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 137108755[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-pyrrolidin-1-yl-tetrahydrofuran-2-yl]methyl benzoate2×

Product 1

HCID 1371087155-amino-3-[(2R,3R,5S)-5-(hydroxymethyl)-3-pyrrolidin-1-yloxolan-2-yl]-6H-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dioneYield 5.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound [(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-pyrrolidin-1-yl-tetrahydrofuran-2-yl]methyl benzoate (compound 32e, 250 mg, 0.54 mmol) in MeOH (8 mL) was added K2CO3 (138 mg, 1.0 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 10.0 mg of 5-amino-3-[(2R,3R,55)-5-(hydroxymethyl)-3-pyrrolidin-1-yl-tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione (Example 32) 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-4b2453cce0a543609ab9aa6e4513b042
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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