HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 6-((5-chloro-2-((l-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)(methyl)amino)hexahydrofuro[3,2-b]furan-3-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-methyl-1H-pyrazol-4-amine | HCID 17354268 | — |
| Reactant | 6-((2,5-Dichloropyrimidin-4-yl)(methyl)amino)hexahydrofuro[3,2-b]furan-3-ol | HCID 118387964 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Product | 6-((5-chloro-2-((l-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)(methyl)amino)hexahydrofuro[3,2-b]furan-3-ol | HCID 118387989 | 38% |
Reaction Conditions
| Temperature | 150 °C |
|---|
Reaction Steps
To a suspension of 6-((2,5-dichloropyrimidin-4-yl)(methyl)amino)hexahydrofuro[3,2-b]furan-3-ol (342.2 mg, 1.12 mmol) and 1-methyl-1H-pyrazol-4-amine hydrochloride (185.0 mg, 1.38 mmol) in n-BuOH (5 mL) was added N-ethyldiisopropylamine (358.8 mg, 2.78 mmol). The reaction mixture was stirred at 150° C. in a sealed tube overnight and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/40) to give the title compound as a beige solid (156 mg, 38.0%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09394281B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-963bf465951a4912a34b1e793166e81f |
| Source note | uspto-grants-2016_07 |