Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Cyanophenylboronic acid | HCID 2734325 | — |
| Reactant | 6-Ethyl-2-(trifluoromethyl)-1H-purine | HCID 45095225 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 11723338 | HCID 11723338 | 19% |
Reaction Steps
A mixture of 6-ethyl-2-trifluoromethylpurine (86 mg, 0.40 mmol), 3-cyanophenylboronic acid (103 mg, 0.70 mmol), copper (II) acetate (72 mg, 0.4 mmol), triethylamine (202 mg, 2.0 mmoL), anhydrous acetonitrile (5 ml) and molecular sieves (˜10 pellets) was stirred at 50-55° C. for 18 hours. Ethyl acetate (20 ml) was added and the solid was filtered off. The filtrate was washed with 20 ml of 5% aqueous sodium bicarbonate, concentrated under vacuum, and purified by chromatography over SiO2 (ethyl acetate/hexane 1:3) to give 24 mg of 9-(3-cyanophenyl)-6-ethyl-2-trifluoromethylpurine (yield 19%). 1H NMR (300 MHz, CDCl3) δ 8.50 (s, 1H), 8.11 (m, 2H), 7.82(m, 2H), 3.35 (q, J=7.5 Hz, 2H), 1.50 (t, J=7.5 Hz, 3H). [ESMS m/z (318.4 (M+H)+)]
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07335654B2 |
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| Source dataset | uspto-grants-2008_02 |
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| ORD ID | ord-3fe03f1bac6a4f8393590cdbf21da877 |
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| Source note | uspto-grants-2008_02 |
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