HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → N-[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentyl]-6-chloropyrimidin-4-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4,6-Dichloropyrimidine | HCID 70943 | — |
| Reactant | (1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentanamine | HCID 59671204 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | N-[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentyl]-6-chloropyrimidin-4-amine | HCID 86618716 | 57.2% |
Reaction Conditions
| Temperature | 140 °C |
|---|
Reaction Steps
To a solution of (1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentanamine (0.400 g, 1.11 mmol) in EtOH (3.0 mL) was added 4,6-dichloro-pyrimidine (0.199 g, 1.33 mmol) and Et3N (0.310 mL, 2.22 mmol). The reaction was heated to 140° C. for 1 h in a sealed tube using microwave irradiation then concentrated in vacuo. The residue was dissolved in CH2Cl2 and purified by flash chromatography (CH2Cl2) to afford the title compound (0.300 g, 57%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08008307B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-b3e07140ce814d518610ad22d2b7ba60 |
| Source note | uspto-grants-2011_08 |