Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Malononitrile | HCID 8010 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-(4,6-Dichloropyrimidin-2-yl)morpholine | HCID 2772068 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86653538 | HCID 86653538 | 111.4% |
Reaction Steps
To a solution of malononitrile (277 mg, 4.2 mmol) in THF cooled to 0° C., sodium hydride (189 mg, 4.7 mmol) was added. When the evolution of gas ceased, 4,6-dichloro-2-morpholinopyrimidine (1aa) (500 mg, 2.1 mmol) was added to the reaction mixture, followed by Pd(PPh3)4. The resulting suspension was refluxed at 80° C. overnight. The mixture was treated with aq. 2M NaOH (10 mL) and stirred for 15 min. The organic layer was discharged and the aqueous was acidified with aq. 2M HCl and extracted with ethyl acetate, yielding 2-(6-chloro-2-morpholinopyrimidin-4-yl)malononitrile (2aa) (617 mg) after drying and solvent evaporation.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08937064B2 |
|---|
| Source dataset | uspto-grants-2015_01 |
|---|
| ORD ID | ord-121c543a287b46febefb116de9635571 |
|---|
| Source note | uspto-grants-2015_01 |
|---|
