Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Acryloyl chloride | HCID 13140 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-(3-Aminophenoxy)-N-(4-(4-methylpiperazin-1-yl)phenyl)thieno[3,2-d]pyrimidin-2-amine | HCID 89547415 | — |
| Solvent | Water | HCID 962 | — |
| Product | Olmutinib | HCID 54758501 | 68.2% |
Reaction Steps
The compound (3.69 mmol) obtained in Step 5 and NaHCO3 (11.07 mmol) were distilled with tetrahydrofuran (40 mL) and distilled water (6 mL), and acryloyl chloride (3.69 mmol) was added thereto slowly at 0° C. with stirring for 15 min. After the reaction was complete, the reaction mixture was distilled with dichloromethane and then washed with sat. NaHCO3 aqueous solution. The organic layer was dried with anhydrous sodium sulfate and then filtered and distilled under a reduced pressure, and the residue was separated by column chromatography (chloroform:methanol=20:1 (volume ratio)) to obtain the title compound (yield: 68.2%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09345719B2 |
|---|
| Source dataset | uspto-grants-2016_05 |
|---|
| ORD ID | ord-6275d1204686462c934eb66da3a02f78 |
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| Source note | uspto-grants-2016_05 |
|---|
