Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Acryloyl chloride | HCID 13140 | — |
| Reactant | HCID 57708355 | HCID 57708355 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 42601891 | HCID 42601891 | 40% |
Reaction Steps
A solution of 3-[6-(3-bromophenylamino)-pyrimidin-4-ylamino]phenylamine (250 mg, 0.7 mmol) and triethylamine (180 mg, 1.75 mmol) in 5 mL of THF was stirred at RT. Acryloyl chloride (80 mg, 0.9 mmol) was added into the reaction mixture and it was stirred at RT for 1 h. The solvent was removed by vacuum evaporation and the crude product was purified by flash chromatography on silica gel with EtOAc/DCM solvent system to afford 115 mg (40% yield) of the title compound as a light colored solid. MS (m/z): MH+=410, 412. 1H NMR (DMSO): 10.15 (s, 1H), 9.36 (s, 1H), 9.28 (s, 1H), 8.34 (s, 1H), 8.02 (s, 1H), 8.00 (s, 1H), 7.51-7.11 (m, 5H), 6.47 (dd, 1H, J1=10.1 Hz, J2=17.0 Hz), 6.27 (dd, 1H, J1=1.9 Hz, J2=17.0 Hz), 6.20 (s, 1H), 5.76 (dd, 1H, J1=10.1 Hz, J2=1.9 Hz) ppm.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09040541B2 |
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| Source dataset | uspto-grants-2015_05 |
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| ORD ID | ord-cf8d7a128a39495c876d27a1c2bb274c |
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| Source note | uspto-grants-2015_05 |
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