HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (1S,2R,3R,5R)-3-(Hydroxymethyl)-5-(5-iodo-6-methoxy-2-(methylthio)pyrimidin-4-ylamino)cyclopentane-1,2-diol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol Hydrochloride | HCID 2734536 | — |
| Reactant | HCID 117677754 | HCID 117677754 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | (1S,2R,3R,5R)-3-(Hydroxymethyl)-5-(5-iodo-6-methoxy-2-(methylthio)pyrimidin-4-ylamino)cyclopentane-1,2-diol | HCID 117677905 | — |
Reaction Conditions
| Temperature | 130 °C |
|---|
Reaction Steps
Compound 3 (5.00 g, 15.7 mmol) and (1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol hydrochloride (Compound 4) (5.80 g, 31.6 mmol) were dissolved in EtOH (50 mL). Triethylamine (6.60 mL, 47.4 mmol) was added, the reaction was sealed, and heated to 130° C. for 18 h. The reaction mixture was cooled to room temperature and concentrated. The residue was purified via column chromatography on silica gel (EtOAc/hexanes) to give the title compound as a colorless oil. LCMS 1.23 min, 428 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09221809B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-6649a51ee5704c4b8bb8c8294eb35f19 |
| Source note | uspto-grants-2015_12 |