Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1-Butanol | HCID 263 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine | HCID 58169118 | — |
| Reactant | HCID 86762625 | HCID 86762625 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86762630 | HCID 86762630 | 80% |
Reaction Steps
A vial was charged with 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-pyrimidin-4-amine (60 mg, 0.25 mmol), N-ethyl-1-(5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)ethanamine (367.0 mg, 1.14 mmol), DIPEA (1.3 mL) and n-BuOH (3.5 mL), sealed and heated at 115° C. for 96 h. The reaction mixture was poured into EtOAc, and the organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by SiO2chromatography to afford 103.9 mg (52.35%) of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-ethyl-N2-(1-(5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)ethyl)pyrimidine-2,4-diamine as a racemic mixture. MS (ESI) m/z: 520.3 [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08815877B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-e81a9d161bce49aeb224799a84a2a031 |
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| Source note | uspto-grants-2014_08 |
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