HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | [(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 | HCID 137108755 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 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 | HCID 137108715 | 5.2% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09441008B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-4b2453cce0a543609ab9aa6e4513b042 |
| Source note | uspto-grants-2016_09 |