Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Acrolein | HCID 7847 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 44450361 | HCID 44450361 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 68647844 | HCID 68647844 | 638.2% |
Reaction Steps
4-[(2,2-Dimethyl-propyl)-(4-iodo-benzyl)-amino]-pyrimidine-2-carbonitrile (0.1 g, 0.2 mmoles), acrolein (0.02 ml, 0.3 mmoles), and triethylamine (0.04 ml, 0.3 mmoles) are dissolved in 5 ml of acetonitrile and Pd(OAc)2 (2.6 mg, 0.012 mmoles) is added at rt. The mixture is stirred at 100° C. for overnight. Water is added and the organic layer is extracted with AcOEt, washed with brine, dried over magnesium sulfate and concentrated. The crude product is purified by silica gel column chromatography to give 423 mg of desired 4-[[4-((E)-2-cyano-vinyl)-benzyl]-(2,2-dimethyl-propyl)-amino]-pyrimidine-2-carbonitrile in 45% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07820818B2 |
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| Source dataset | uspto-grants-2010_10 |
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| ORD ID | ord-224fc9820ea441e89c0c55488d899ded |
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| Source note | uspto-grants-2010_10 |
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