Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | Chloroiodomethane | HCID 11644 | — |
| Reactant | n-Butyl lithium | HCID 61028 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | ethyl trans-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropanecarboxylate | HCID 86732076 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Lithium diisopropylamide | HCID 2724682 | — |
| Product | 2-chloro-1-((1S,2S)-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)ethanone | HCID 90157013 | — |
Reaction Steps
A 2 M solution of lithium diisopropylamide (LDA) was prepared by the addition of N-butyllithium (8.0 mL, 2.5 M, 20 mmol) to diisopropylamine (2.4 g, 24 mmol) in THF (2 mL) at 0° C. After stirring for 1 h, the LDA solution (6.6 mL, 13.2 mmol) was added to a flask containing 1-4 (1.0 g, 3.3 mmol) and chloroiodomethane (2.9 g, 17 mmol) in THF (33 mL) at −78° C. The mixture was stirred at −78° C. for 2 h then warmed to room temperature and diluted with EtOAc (30 mL). The solution was washed with saturated aqueous sodium bicarbonate (2×20 mL) and brine (1×20 mL) and the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography (20-40% EtOAc/hexanes) to afford 1-5 as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09359348B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-6e3d48de0af2466180cbe069eb4bfb57 |
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| Source note | uspto-grants-2016_06 |
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