HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (1R,2S,3R,5R)-3-[(6-chloropyrimidin-4-yl)amino]-5-(hydroxymethyl)cyclopentane-1,2-diol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4,6-Dichloropyrimidine | HCID 70943 | — |
| Reactant | (1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol Hydrochloride | HCID 2734536 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | (1R,2S,3R,5R)-3-[(6-chloropyrimidin-4-yl)amino]-5-(hydroxymethyl)cyclopentane-1,2-diol | HCID 59671293 | 90.1% |
Reaction Conditions
| Temperature | 150 °C |
|---|
Reaction Steps
A mixture of (1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol hydrochloride (2.00 mg, 1.09 mmol), 4,6-dichloropyrimidine (240. mg, 1.61 mmol) and Et3N (0.380 mL, 2.73 mmol) in EtOH (3.00 mL) was heated to 150° C. for 15 min using MWI. The crude mixture was purified via silica gel chromatography eluting with a gradient of 0 to 15% MeOH in DCM to afford the title compound (255 mg, 90%). LC/MS: Rt=1.13 min, ES+ 260. (AA standard).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08008307B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-6c5834b16db849af88e9dd4fa09dba71 |
| Source note | uspto-grants-2011_08 |