HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → Methyl 2-(4-methyl-6-(naphthalen-2-yl)-2-phenylpyrimidin-5-yl)pentanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (Naphthalen-2-yl)boronic acid | HCID 2734375 | — |
| Reactant | Methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate | HCID 86665652 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Water 1,2-dimethoxyethane | HCID 18180031 | — |
| Product | Methyl 2-(4-methyl-6-(naphthalen-2-yl)-2-phenylpyrimidin-5-yl)pentanoate | HCID 66955496 | 71.6% |
Reaction Steps
This compound was prepared according to general method E from methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.159 g; 0.5 mmol), tetrakis(triphenylphosphine) palladium(0) (0.058 mg; 0.05 mmol), N,N-Diisopropylethylamine (0.345 mL; 2 mmol) and naphthalen-2-ylboronic acid (0.258 g; 1.5 mmol) in DME-water (2 mL) for 30 min. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-40%) in heptane furnished 0.147 g (71%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08906906B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-6ecd724fc9714c3eaae826d4b704bb2c |
| Source note | uspto-grants-2014_12 |