Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | tert-Butyl methyl ether | HCID 15413 | — |
| Reactant | (6-Chloro-5-methylpyridin-3-yl)methanol | HCID 11686949 | — |
| Reactant | HCID 178418546 | HCID 178418546 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58001709 | HCID 58001709 | 62.8% |
Reaction Steps
CuCN (54.3 mg, 0.607 mmol) was added to a solution of (6-chloro-5-methyl-3-pyridinyl)methanol (47.8 mg, 0.303 mmol) in anhydrous DMF (2 ml) and the mixture was stirred under microwave irradiation at 250° C. for 35 min. Full conversion was observed by HPLC. TBME and 28% NH3 were added. Extraction, drying (MgSO4), filtration, and removal of the solvent afforded 5-(hydroxymethyl)-3-methyl-2-pyridinecarbonitrile (28.2 mg, 0.190 mmol, 62.8% yield) pure enough to be used in the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08097628B2 |
|---|
| Source dataset | uspto-grants-2012_01 |
|---|
| ORD ID | ord-2318b111d61e457d85375852ba3044b8 |
|---|
| Source note | uspto-grants-2012_01 |
|---|
