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

HRID 60758Notes

Reaction equation

HRID 60758 reaction equation
[C:1]([O:9][CH2:10][C@@H:11]1[CH2:15][C@@H:14]([O:16]C(=O)C)[C@H:13]([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:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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:13]3[C@H:14]([OH:16])[CH2:15][C@@H:11]([CH2:10][OH:9])[O:12]3)[C:24]=2[N:25]=1.[C:1]([O:9][CH2:10][C@@H:11]1[CH2:15][C@@H:14]([OH:16])[C@H:13]([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:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 137108751[(2S,4R,5R)-4-acetoxy-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-2-yl]methyl benzoate2×

Product 2

HCID 1355255055-amino-3-[(2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dioneHCID 137108701[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]methyl benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [(2S,4R,5R)-4-acetoxy-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-2-yl]methyl benzoate (compound 38a, 4.72 g, 10.6 mmol) and potassium carbonate (1.46 g, 10.6 mmol) in methanol (106 mL) was stirred at room temperature for 3.5 hours. The reaction was quenched by addition of acetic acid (1.5 mL). The resulting mixture was concentrated in vacuo to remove the solvent and the residue was purified by column chromatography on silica gel (eluting with 0-5% methanol in DCM) to afford 1.0 g of 5-amino-3-[(2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione (compound 38b) and 2.8 g of [(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]methyl benzoate (compound 38c) as a pale solid.

Workup

  1. customThe reaction was quenched by addition of acetic acid (1.5 mL)
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. customto remove the solvent
  4. customthe residue was purified by column chromatography on silica gel (eluting with 0-5% methanol in DCM)

Sources & evidence

ORD record
ord-3383431c0ccf47238d3915112f62f6b9
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

Loading…