HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyanamide → (Rac)-[[3-({4-[2-(benzyloxy)-4-fluorophenyl]-5-fluoropyrimidin-2-yl}amino)benzyl](methyl)-lambda4-sulfanylidene]-cyanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyanamide | HCID 9864 | — |
| Reactant | N-Bromophthalimide | HCID 75542 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | 4-[2-(Benzyloxy)-4-fluorophenyl]-5-fluoro-N-{3-[(methylsulfanyl)methyl]phenyl}pyrimidin-2-amine | HCID 89444601 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium Thiosulfate | HCID 24477 | — |
| Product | (Rac)-[[3-({4-[2-(benzyloxy)-4-fluorophenyl]-5-fluoropyrimidin-2-yl}amino)benzyl](methyl)-lambda4-sulfanylidene]-cyanamide | HCID 89444507 | — |
Reaction Steps
2-Bromo-1H-isoindole-1,3(2H)-dione (22.0 mg; 0.12 mmol) was added to a solution of 4-[2-(benzyloxy)-4-fluorophenyl]-5-fluoro-N-{3-[(methylsulfanyl)methyl]phenyl}pyrimidin-2-amine (37.0 mg; 0.08 mmol), cyanamide (4.5 mg; 0.11 mmol) and potassium 2-methylpropan-2-olate (11.1 mg; 0.10 mmol) in MeOH (0.44 mL) at RT. The batch was stirred for 4 hours before it was diluted with DCM and aqueous sodium thiosulfate solution. The batch was extracted with DCM (2×). The combined organic phases were filtered using a Whatman filter and concentrated to give crude (rac)-[[3-({4-[2-(benzyloxy)-4-fluorophenyl]-5-fluoropyrimidin-2-yl}amino)benzyl](methyl)-λ4-sulfanylidene]-cyanamide that was used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09133171B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-2e9f6b7f2e684585bd52bdc6bb16603e |
| Source note | uspto-grants-2015_09 |